Chloroform → N-{[(7H-Purin-6-yl)sulfanyl]methyl}benzamide

反応式

ClC[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6].[SH:12][C:13]1[N:21]=[CH:20][N:19]=[C:18]2[C:14]=1[NH:15][CH:16]=[N:17]2.[CH:22](Cl)(Cl)Cl>>[C:5]([NH:7][CH2:22][S:12][C:13]1[N:21]=[CH:20][N:19]=[C:18]2[C:14]=1[NH:15][CH:16]=[N:17]2)(=[O:6])[C:4]1[CH:3]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

反応物 3

HCID 6212Chloroform

HCID 222911382-(Chloromethyl)benzamide2 回

HCID 178527888HCID 178527888、化合物

生成物 1

HCID 13314913N-{[(7H-Purin-6-yl)sulfanyl]methyl}benzamide

実験手順

Chloromethylbenzamide (55.71 mg, 0.328 mmol) and 6-mercaptopurine (50 mg, 0.328 mmol) were dissolved in 1.5 ml of dry DMSO-d6 to give a clear yellow solution. The progress of the reaction was followed by monitoring changes in the NMR spectrum. The doublet at 5.42, due to chloromethylbenzamide, had completely disappeared after 10 hours and a new doublet at 5.83 indicated the presence of the benzamidomethylthio moiety. Chloroform was added which caused a yellow gum to precipitate which was washed several times with chloroform and crystallized from methanol: mp 197°-200° C.; IR (KBR) 1720 cm-1 ; NMR (pyridin-d5) δ8.39-7.35 (m, 5, aryl), 5.99 (d, 2, --SCH2NH--); MS m/e 285 (M+).