Phosgene → 8-chlorodibenz[b,f][1,4]thiazepine-10(11H)-carbonyl chloride

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([NH2:12])[CH:11]=1.[CH2:20](N(CC)CC)C>O1CCCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][N:12]([C:1]([Cl:4])=[O:2])[C:10]=2[CH:11]=1

Participants

Procedure

To a cold (ice-H2O bath), stirred solution of phosgene (1.93M in toluene; 8.6 mL) in anhydrous tetrahydrofuran (40 mL) under a nitrogen atmosphere is added, dropwise, a solution of the title product of Example 48 (2.00 g) and triethylamine (1.3 mL) in anhydrous tetrahydrofuran (30 mL). The resulting mixture is stirred at room temperature for 90 minutes, and the solvent is then evaporated in vacuo to provide the title product.