3'-Ethylamino-4'-nitroacetanilide → N-{4-[3-Benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-3-ethylaminophenyl}acetamide

HRID 2121945Notes

Reaction equation

HRID 2121945 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:7][C:8](=[O:10])[CH3:9])[CH3:2].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>>[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][C:36]1=[N:14][C:13]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[NH:3][CH2:1][CH3:2])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

2

Reactant 1

HCID 219374493'-Ethylamino-4'-nitroacetanilide

Product 1

HCID 73855023N-{4-[3-Benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-3-ethylaminophenyl}acetamide

Procedure

In a manner similar to Example 30, intermediate 3′-ethylamino-4′-nitroacetanilide 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 7.45-7.53 (3H, m), 7.27-7.37 (4H, m), 7.17 (1H, m), 7.03-7.09 (2H, m), 6.91 (1H, d), 6.83 (1H, br d), 6.75 (1H, br s), 5.18 (2H, s), 3.78 (3H, s), 2.99 (2H, m), 2.15 (3H, s), 1.03 (3H, t); MS(ESI): 530 (MH+).

Sources & evidence

ORD record
ord-c4ddf5e6eeba4478bc87f78d2243d5d4
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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