Ethyl Thioglycolate → HCID 723916, compound

HRID 1764620Notes

Reaction equation

HRID 1764620 reaction equation
[Na].[SH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([CH3:17])[N:11]=1>CCO>[NH2:9][C:10]1[N:15]=[C:14]([S:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 5360545Sodium

Product 1

HCID 723916HCID 723916, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (4.6 g, 0.2 mol) was dissolved in 1 l. abs. EtOH. Ethyl mercaptoacetate (24 g, 0.2 mol) was added and the resultant mixture was stirred 1 hr. at room temperature. The 2-amino-4-chloro-6-methylpyrimidine (0.2 mol) was added and the mixture was heated at reflux for 18 hrs. The reaction mixture was evaporated to a syrupy residue which was portitioned between CHCl3 (1.5 l.) and H2O (100 ml). The CHCl3 phase was dried (MgSO4) and evaporated to give the crude product as an oil, 40.6 g (91%). The straw colored oil crystallized upon standing, m.p. 65°-69°. The analytical sample was obtained by a recrystallization from cyclohexane, 27 g (60%), m.p. 71°-73°.

Workup

  1. customat room temperature
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 18 hrs
  4. customThe reaction mixture was evaporated to a syrupy residue which
  5. dry with materialThe CHCl3 phase was dried (MgSO4)
  6. customevaporated
  7. customto give the crude product as an oil, 40.6 g (91%)
  8. customThe straw colored oil crystallized
  9. customThe analytical sample was obtained by a recrystallization from cyclohexane, 27 g (60%), m.p. 71°-73°

Sources & evidence

ORD record
ord-a4cdd392c31a4bee992da9c6425be440
Source dataset
uspto-grants-1978_09
Patent number
US04117131

Reaction notes

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