1-Methyl-2-methylthioquinolinium p-toluenesulfonate → 3-[3-Benzyl-5-(1-methyl-1H-quinolin-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzonitrile

HRID 1241982Notes

Reaction equation

HRID 1241982 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:12][N+:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1SC.[CH2:25]([N:32]1[C:36](=[O:37])[CH2:35][S:34][C:33]1=[N:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[NH:47][CH2:48][CH3:49])[C:42]#[N:43])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:32]1[C:36](=[O:37])[C:35](=[C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]2[CH3:12])[S:34][C:33]1=[N:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[NH:47][CH2:48][CH3:49])[C:42]#[N:43])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 155970931-Methyl-2-methylthioquinolinium p-toluenesulfonateHCID 219373763-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile

Product 1

HCID 738550193-[3-Benzyl-5-(1-methyl-1H-quinolin-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzonitrile

Procedure

In a manner similar to Example 45, intermediate 1-methyl-2-methylthioquinolinium p-toluenesulfonate was condensed with 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile to afford the title compound. 1H-NMR (CDCl3): δ 7.41–7.58 (4H, m), 7.20–7.38 (9H, m), 6.49 (1H, d), 5.16 (2H, s), 3.79 (3, brs), 3.01 (2H, q), 1.02 (3H, t); MS(ESI): 492 (MH+).

Sources & evidence

ORD record
ord-2a115ff04ba74060b3a8760c5da6e590
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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