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Chapter – 3 Preparation of small library…..
9. Peak obtained at 161.61 δ ppm is due to the azomethine carbon C10.
10. Carbonyl carbon (C9) of indolinone ring became deshielded due to the
adjacent nitrogen atom and showed peak in down field at 173.69 δ
ppm.
11. Carbonyl carbon of amide group in hydrazide linkage (C20) became
most deshielded and showed peak in down field at 179.30 δ ppm.
1 H NMR spectral interpretation of 3-(1, 3-benzothiazol-2-ylimino)-1-
(morpholin-4-ylmethyl)-1, 3-dihydro-2H-indol-2-one (DNJ-1401)
1. Four protons of two methylene groups (C23 & C27) of morpholine ring
gave triplet at 2.36 δ ppm.
2. Another four protons of two methylene groups (C24 & C26) of
morpholine ring gave triplet at 2.60 δ ppm.
3. Two protons of methylene group (C21) gave singlet at 3.76 δ ppm.
4. Rests of the peaks are due to the aromatic protons which are obtained
as multiplet and are in the agreement of the structure of the molecule.
Two protons of C7 and C19 gave quintet at 6.97 δ ppm. Two protons of
C8 and C18 gave triplet at 7.11 δ ppm, while one proton of C16 gave
multiplet at 7.33 δ ppm. Rests of the three protons of C6, C9 and C17
gave multiplet at 7.43 δ ppm.
13 C NMR spectral interpretation of 3-(1, 3-benzothiazol-2-ylimino)-1-
(morpholin-4-ylmethyl)-1, 3-dihydro-2H-indol-2-one (DNJ-1401)
1. Two methylene carbons (C23 & C27) of morpholinyl ring gave peak at
46.55 δ ppm. While another two methylene carbons of morpholinyl ring
(C24 & C26) showed peak at 66.89 δ ppm.
2. Methylene carbon (C21) attached to both the nitrogen of indole nucleus
and morpholine nucleus gave peak at 66.66 δ ppm.
3. Peaks obtained at 76.89, 77.21, 77.53 δ ppm are due to the solvent
CDCl3.
Department of Chemistry, Saurashtra University, Rajkot – 360 005 169