Methyl 4-(ethylamino)-3-nitrobenzoate → 3-[3-Benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzoic Acid Methyl Ester

HRID 1241965Notes

Reaction equation

HRID 1241965 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([N+:13]([O-])=O)[CH:5]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:28]([N:35]1[C:39](=[O:40])[C:38](=[C:41]2[N:45]([CH3:46])[C:44]3[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=3[S:42]2)[S:37][CH2+:36]1SC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([N:13]=[C:36]2[N:35]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:39](=[O:40])[C:38](=[C:41]3[N:45]([CH3:46])[C:44]4[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=4[S:42]3)[S:37]2)[CH:5]=1

Participants

2

Reactant 1

HCID 20626654Methyl 4-(ethylamino)-3-nitrobenzoate

Product 1

HCID 738550603-[3-Benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzoic Acid Methyl Ester

Procedure

In a manner similar to Example 30, intermediate 4-ethylamino-3-nitrobenzoic acid methyl ester was hydrogenated and then condensed with 3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate to afford the title compound. 1H-NMR (CDCl3): δ 7.73 (1H, dd), 7.65 (1H, d), 7.52 (1H, dd), 7.45–7.49 (2H, m), 7.27–7.38 (4H, m), 7.18 (1H, m), 7.06 (1H, d), 6.52 (1H, d), 5.19 (2H, s), 4.14 (1H, br t), 3.85 (3H, s), 3.78 (3H, s), 3.04 (2H, m), 1.04 (3H, t); MS(ESI): 531 (MH+).

Sources & evidence

ORD record
ord-2f2a3091e9dd4dcbb9d6741b16ba632a
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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