Triethylamine → N-(4-chloro-2-methyl-benzothiazol-5-yl)-3-methoxy-benzamide

HRID 1766329Notes

Reaction equation

HRID 1766329 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:12].[C:13](Cl)(=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 112178574-Chloro-2-methylbenzo[d]thiazol-5-amine

Product 1

HCID 21110275N-(4-chloro-2-methyl-benzothiazol-5-yl)-3-methoxy-benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 4-chloro-2-methyl-benzothiazol-5-ylamine (50 mg, 0.25 mmol) in THF (1.5 mL) with m-anisoyl chloride (41 μL, 0.30 mmol) in presence of triethylamine (42 μL, 0.30 mmol) according to method A gave N-(4-chloro-2-methyl-benzothiazol-5-yl)-3-methoxy-benzamide (70 mg, 0.21 mmol, 84% yield) as a orange powder after crystallisation in hexane/DCM.

Sources & evidence

ORD record
ord-8e566e78d6f54ebaac5c93ca394848a5
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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