2,2,2-Trichloroethyl chloroformate → (2-Benzoylamino-4-methoxy-benzothiazol-7-yl)-(4-methyl-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 51864

Reaction equation

[CH3:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7](CC2C=CC(C)=CC=2)[C:8]2[C:16]3[S:15][C:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:13][C:12]=3[C:11]([O:26][CH3:27])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:39]([O:41][CH2:42][C:43]([Cl:46])([Cl:45])[Cl:44])=[O:40]>C(#N)C>[Cl:44][C:43]([Cl:46])([Cl:45])[CH2:42][O:41][C:39](=[O:40])[N:7]([C:8]1[C:16]2[S:15][C:14]([NH:17][C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:13][C:12]=2[C:11]([O:26][CH3:27])=[CH:10][CH:9]=1)[CH2:6][C:5]1[CH:36]=[CH:37][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 300 mg (0.59 mmol) N-{7-[bis-(4-methyl-benzyl)-amino]-4-methoxy-benzothiazol-2-yl}-benzamide in 10 ml acetonitrile was added dropwise 0.60 ml (4.46 mmol) 2,2,2-trichloroethyl chloroformate and the reaction mixture heated at 80° C. for 72 h. The mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate/hexane) afforded 138 mg (40%) (2-benzoylamino-4-methoxy-benzothiazol-7-yl)-(4-methyl-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester as a yellow solid. ES-MS m/e (%):584 (M{37Cl, 37Cl, 37Cl}+H+, 5), 582 (M{37Cl, 37Cl, 35Cl}+H+, 32), 580 (M{37Cl, 35Cl, 35Cl}+H+, 100), 578 (M{35Cl, 35Cl, 35Cl}+H+, 92).

Workup

concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-72ea1724071f4980b0661692dda3e538
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713499B2

Linked notes

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