Hydrochloric Acid → Ethyl {[6-(4-Fluorophenoxy)-2-benzothiazolyl]amino}methanethioate

반응식

[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[C:20]([O:22][CH3:23])=[S:21].Cl.N1C=CC=C[CH:26]=1>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:20](=[S:21])[O:22][CH2:23][CH3:26])[S:3][C:4]=3[CH:10]=2)=[CH:17][CH:16]=1

참가 물질

반응물 4

HCID 313Hydrochloric Acid

HCID 1049Pyridine

HCID 554404Methyl chloromethanethioate

HCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazole

생성물 1

HCID 86588974Ethyl {[6-(4-Fluorophenoxy)-2-benzothiazolyl]amino}methanethioate수율 65%

실험 절차

A suspension of 2-amino-6-(4′-fluorophenoxy)-benzothiazole (associated with 2.0 eq of KBr salt, 2.50 g, 5.02 mmol) in 10 mL pyridine was treated dropwise with methyl chlorothioformate (0.65 mL, 7.53 mmol, 01.5 eq). It was stirred at room temperature for about 1 hour, and was poured into 40 mL ice water. The mixture was acidified slowly with 1 M HCl solution. The result precipitate was filtered off, washed with water and MeOH, and dried under vacuum to give 1.18 g (65%) desired compound. LC/MS 334.9 (M+1); LC retention time 3.70 min.