2-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfonate → 2-(5-Acetyl-2-ethylaminophenylimino)-5-[5-(2-chloroethoxy)-3-methyl-3H-benzothiazol-2-ylidene]-3-furan-2-ylmethylthiazolidin-4-one

HRID 2121978Notes

Reaction equation

HRID 2121978 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(OC2C(C(C)C)CCC(C)C2)(=O)=O)=CC=1.[C:37]([C:40]1[CH:41]=[CH:42][C:43]([NH:59][CH2:60][CH3:61])=[C:44]([N:46]=[C:47]2[N:51]([CH2:52][C:53]3[O:54][CH:55]=[CH:56][CH:57]=3)[C:50](=[O:58])[CH2:49][S:48]2)[CH:45]=1)(=[O:39])[CH3:38]>>[C:37]([C:40]1[CH:41]=[CH:42][C:43]([NH:59][CH2:60][CH3:61])=[C:44]([N:46]=[C:47]2[N:51]([CH2:52][C:53]3[O:54][CH:55]=[CH:56][CH:57]=3)[C:50](=[O:58])[C:49](=[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:48]2)[CH:45]=1)(=[O:39])[CH3:38]

Participants

4

Reactant 3

HCID 5866292-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfonateHCID 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 menthyl 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-7ae43a8ebaa749aba04d2ca16c5dc37f
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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