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

HRID 1766330Notes

Reaction equation

HRID 1766330 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].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22](Cl)=[O:23])[CH:18]=[CH:19][CH:20]=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:22](=[O:23])[CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332463-Methoxyphenylacetyl chlorideHCID 112178574-Chloro-2-methylbenzo[d]thiazol-5-amine

Product 1

HCID 21110334N-(4-chloro-2-methyl-benzothiazol-5-yl)-2-(3-methoxy-phenyl)-acetamideYield 48%

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 3-methoxyphenylacetyl chloride (47 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)-2-(3-methoxy-phenyl)-acetamide (40 mg, 0.11 mmol, 48% yield) as a white powder after crystallisation in hexane/DCM.

Sources & evidence

ORD record
ord-7be76951b81a40eeac9a8c495b24dd6e
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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