Carbon Dioxide → HCID 22155484, compound

Reaction equation

B(Br)(Br)Br.[CH3:5][NH:6][S:7]([C:10]1[S:11][C:12]2[CH:18]=[C:17]([O:19]CC)[CH:16]=[CH:15][C:13]=2[N:14]=1)(=[O:9])=[O:8].C(=O)=O>C(Cl)Cl>[OH:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([S:7]([NH:6][CH3:5])(=[O:8])=[O:9])[S:11][C:12]=2[CH:18]=1

Participants

Procedure

A one molar solution of boron tribromide in CH2Cl2 (21 mL) was cooled to -76° C. in a dry ice/acetone bath. N-Methyl-6-ethoxy-2-benzothiazole-sulfonamide (1, og.; 0.0037 mol) was added and the reaction stirred in the dry ice bath for four hours. The reaction was removed, stirred at room temperature for 18 hours, poured into a mixture of 25 mL of crushed ice/25 mL water and stirred for 30 minutes. The crude material was collected and purified by dissolving in 10% Na2CO3, filtered, anc precipitated with dilute acetic acid (1:1) to give 0.75g (83.0% yield) of pure product, m.p. 189°-190° C.; NMR(DMSO-d ) delta 8.5-8.0(m, 3H); 7.6(d, lH); 7.4-7.2 (q, lH).