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

HRID 325846Notes

Reaction equation

HRID 325846 reaction equation
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

Participants

4

Reactant 3

HCID 6212ChloroformHCID 222911382-(Chloromethyl)benzamide2×HCID 178527888HCID 178527888, compound

Product 1

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

Procedure

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+).

Workup

  1. customto give a clear yellow solution
  2. customto precipitate which
  3. washwas washed several times with chloroform
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-c35661f87b564f9998712b87d2a5b173
Source dataset
uspto-grants-1984_04
Patent number
US04443435

Reaction notes

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