Chloroacetamide → 2-[(6,9-Dimethyl-9H-purin-2-yl)sulfanyl]acetamide

HRID 1448481Notes

Reaction equation

HRID 1448481 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]=[CH:5][N:6]([CH3:12])[C:7]=2[NH:8][C:9](=[S:11])[N:10]=1.Cl[CH2:14][C:15]([NH2:17])=[O:16].C(=O)([O-])O.[Na+]>O>[C:15]([CH2:14][S:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[CH3:12])=[C:2]([CH3:1])[N:10]=1)(=[O:16])[NH2:17]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 178433552HCID 178433552, compound

Product 1

HCID 3315022-[(6,9-Dimethyl-9H-purin-2-yl)sulfanyl]acetamideYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6,9-Dimethylpurine-2-(3H)-thione (0.45 g), chloroacetamide (0.3 g), sodium hydrogen carbonate (0.25 g), and water (10 ml) were heated under reflux for 1 hr. Refrigeration gave a solid which recrystallised from water to give the carbamoylmethylthiopurine (0.40 g), m.p. 163°-164° (Found: C, 45.3; H, 4.9; N, 29.2. C9H11N5OS requires C, 45.6; H, 4.7; N, 29.5%).

Workup

  1. temperatureunder reflux for 1 hr
  2. customRefrigeration gave a solid which
  3. customrecrystallised from water

Sources & evidence

ORD record
ord-b7169f54fc3241b99a8a1bd6228cef34
Source dataset
uspto-grants-1979_12
Patent number
US04180576

Reaction notes

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