Methyl p-toluenesulfonate → 2-(5-Acetyl-2-ethylaminophenylimino)-3-benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)imidazolidin-4-one

HRID 1241989Notes

Reaction equation

HRID 1241989 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[N:10]([CH3:24])[C:9]1=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(OC)(=O)=O)=CC=1.[NH2:38][C:39]1[CH:40]=[C:41]([C:48](=[O:50])[CH3:49])[CH:42]=[CH:43][C:44]=1[NH:45][CH2:46][CH3:47]>>[C:48]([C:41]1[CH:42]=[CH:43][C:44]([NH:45][CH2:46][CH3:47])=[C:39]([N:38]=[C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12](=[O:13])[C:11](=[C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[S:15]3)[N:10]2[CH3:24])[CH:40]=1)(=[O:50])[CH3:49]

Participants

4

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 219373693'-Amino-4'-(ethylamino)acetophenoneHCID 726398863-Benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxoimidazolidin-4-one

Product 1

HCID 673696082-(5-Acetyl-2-ethylaminophenylimino)-3-benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)imidazolidin-4-one

Procedure

In a manner similar to Example 1, intermediate 3-benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxoimidazolidin-4-one was alkylated with methyl p-toluenesulfonate and condensed with 3′-amino-4′-ethylaminoacetophenone to yield the title compound. 1H-NMR (CDCl3): δ 8.11 (1H, d), 7.84 (1H, dd), 7.51 (1H, dd), 7.31 (1H, m), 7.16 (1H, m), 6.95–7.12 (7H, m), 6.08 (1H, br t), 4.46 (2H, hs m), 3.99 (2H, m), 3.78 (3H, s), 3.50 (3H, s), 2.65 (3H, s), 1.06 (3H, t); MS(ESI): 512 (MH+).

Sources & evidence

ORD record
ord-70c5a9dd72284d088555931ef67f30b4
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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