Thionyl Chloride → 8-Chloro-4-[3-(4-chloromethyl-thiazol-2-yl)-phenyl]-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265919Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:27]([CH3:29])[CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[S:19][CH:20]=[C:21]([CH2:23]O)[N:22]=4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1.S(Cl)([Cl:32])=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:27]([CH3:29])[CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][Cl:32])[N:22]=4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 8-chloro-7-dimethylamino-4-[3-(4-hydroxymethyl-thiazol-2-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one (0.38 g) (Example 19) and thionyl chloride (0.1 mL) in CH2Cl2 was heated to 40° C. for 2 h. The heterogeneous mixture was evaporated in vacuum and the residue was triturated with AcOEt to give the title compound (0.44 g) as a light-brown solid, MS (ISP) 445.1 [(M+H)+].

Workup

customThe heterogeneous mixture was evaporated in vacuum
customthe residue was triturated with AcOEt

Sources & evidence

ORD record: ord-f61b9fcf60604afba56630d10a37a03e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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