4-(Chloromethyl)benzoyl chloride → 4-chloromethyl-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

HRID 51845

Reaction equation

HRID 51845 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]([CH2:15][CH2:16][O:17][CH3:18])[CH3:14])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C1COCC1.ClCCl>[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:12][C:10]2[S:11][C:7]3[C:6]([N:13]([CH2:15][CH2:16][O:17][CH3:18])[CH3:14])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 220157444-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

Product 1

HCID 102164874-chloromethyl-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamideYield 42.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 300 mg (1.12 mmol) 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine and 1.12 ml (6.56 mmol) N-ethyldiisopropylamine in 10 ml THF at room temperature was added dropwise a solution of 257 mg (1.36 mmol) 4-(chloromethyl)-benzoyl chloride in 3 ml dichloromethane and stirring continued at room temperature for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether and hexane afforded 200 mg (42%) 4-chloromethyl-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide as a light yellow crystalline solid. ES-MS m/e (%): 422 (M{37Cl}+H+, 32), 420 (M{35Cl}+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-5d5ede813284486dbafb3c5d5c933bb6
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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