Methyl p-toluenesulfonate → 2-[2'-(5-Acetyl-2-ethylaminophenylimino)-3'-benzyl-5-methyl-4'-oxo-4-phenyl-3',4'-dihydro-2'H-[2,5']bithiazolyliden-3-yl]ethyl Acetate

HRID 2122001Notes

Reaction equation

HRID 2122001 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH3:18])[S:9][C:8]1=S)(=[O:3])[CH3:2].C1(C)C=CC(S(OC)(=O)=O)=CC=1.[C:32]([C:35]1[CH:36]=[CH:37][C:38]([NH:55][CH2:56][CH3:57])=[C:39]([N:41]=[C:42]2[N:46]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:45](=[O:54])[CH2:44][S:43]2)[CH:40]=1)(=[O:34])[CH3:33]>>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH3:18])[S:9][C:8]1=[C:44]1[S:43][C:42](=[N:41][C:39]2[CH:40]=[C:35]([C:32](=[O:34])[CH3:33])[CH:36]=[CH:37][C:38]=2[NH:55][CH2:56][CH3:57])[N:46]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:45]1=[O:54])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 219375452-(5-Methyl-4-phenyl-2-thioxothiazol-3-yl)ethyl AcetateHCID 219375832-(5-Acetyl-2-ethylaminophenylimino)-3-benzylthiazolidin-4-one

Product 1

HCID 736903972-[2'-(5-Acetyl-2-ethylaminophenylimino)-3'-benzyl-5-methyl-4'-oxo-4-phenyl-3',4'-dihydro-2'H-[2,5']bithiazolyliden-3-yl]ethyl Acetate

Procedure

In a manner similar to that described in Example 52, intermediate 2-(5-methyl-4-phenyl-2-thioxothiazol-3-yl)ethyl acetate was alkylated with methyl p-toluenesulfonate and condensed with 2-(5-acetyl-2-ethylaminophenylimino)-3-benzylthiazolidin-4-one to yield the title compound. 1H-NMR (CDCl3): δ 7.63-7.67 (2H, m), 7.44-7.51 (5H, m), 7.28-7.37 (5H, m), 6.50 (1H, d), 5.19 (2H, s), 4.30 (1H, br t), 4.03 (4H, m), 3.06 (2H, m), 2.48 (3H, s), 2.05 (3H, s), 1.89 (3H, s), 1.05 (3H, t); MS(ESI): 627 (MH+).

Sources & evidence

ORD record
ord-27f0780f66c846d6b6ec0344aa1b5cc2
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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