Methyl p-toluenesulfonate → 2-(5-Acetyl-2-ethylaminophenylimino)-5-[5-(2-chloroethoxy)-3-methyl-3H-benzothiazol-2-ylidene]-3-furan-2-ylmethylthiazolidin-4-one

HRID 1242009Notes

Reaction equation

HRID 1242009 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](SC)=[N:10][C:9]=2[CH:15]=1.[C:16]1(C)C=CC(S(OC)(=O)=O)=CC=1.[C:28]([C:31]1[CH:32]=[CH:33][C:34]([NH:50][CH2:51][CH3:52])=[C:35]([N:37]=[C:38]2[N:42]([CH2:43][C:44]3[O:45][CH:46]=[CH:47][CH:48]=3)[C:41](=[O:49])[CH2:40][S:39]2)[CH:36]=1)(=[O:30])[CH3:29]>>[C:28]([C:31]1[CH:32]=[CH:33][C:34]([NH:50][CH2:51][CH3:52])=[C:35]([N:37]=[C:38]2[N:42]([CH2:43][C:44]3[O:45][CH:46]=[CH:47][CH:48]=3)[C:41](=[O:49])[C:40](=[C:11]3[N:10]([CH3:16])[C:9]4[CH:15]=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[CH:6]=[CH:7][C:8]=4[S:12]3)[S:39]2)[CH:36]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 219374875-(2-Chloroethoxy)-2-methylthio-benzothiazoleHCID 219375112-(5-Acetyl-2-ethylaminophenylimino)-3-furan-2-ylmethyl-thiazolidin-4-one

Product 1

HCID 738551402-(5-Acetyl-2-ethylaminophenylimino)-5-[5-(2-chloroethoxy)-3-methyl-3H-benzothiazol-2-ylidene]-3-furan-2-ylmethylthiazolidin-4-one

Procedure

In a manner similar to Example 45, intermediate 5-(2-chloroethoxy)-2-(methylthio)benzothiazole was alkylated with methyl p-toluenesulfonate and then condensed with the above 2-(5-acetyl-2-ethylaminophenylimino)-3-furan-2-ylmethyl-thiazolidin-4-one. MS(ESI): 583 (MH+).

Sources & evidence

ORD record
ord-c3b668bf83bd423da5a3f7f1e827297d
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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