Benzyl mercaptan → HCID 20475694, compound

HRID 905221Notes

Reaction equation

HRID 905221 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][SH:18])=[CH:13][CH:12]=1.CC[O-].[Na+]>C(O)C>[CH2:17]([S:18][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 2723922Sodium ethoxideHCID 125019865-Bromo-2-chloro-4,6-dimethylpyrimidine

Product 1

HCID 20475694HCID 20475694, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4,6-dimethyl-5-bromopyrimidine (10 mmol) was added to a solution of benzylthiol (11 mmol) and 0.138 M NaOEt in ethanol (80 ml). The mixture was stirred at room temperature for 70 min and then heated under reflux for 40 min. The solvent was then distilled off, the residue extracted with chloroform (50 ml), the chloroform solution washed with 2 M NaOH and the dried (MgSO4) solution evaporated to leave the sulfide which was purified by distillation; yield 94%, b.p. 232°-234° C./15 mmHg. 1H NMR (Cl3CF): δ2.50 (Me-4, Me-6), 4.26 (CH2), 7.20 (Ph).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 min
  3. distillationThe solvent was then distilled off
  4. extractionthe residue extracted with chloroform (50 ml)
  5. washthe chloroform solution washed with 2 M NaOH
  6. dry with materialthe dried (MgSO4) solution
  7. customevaporated

Sources & evidence

ORD record
ord-eb44e0c4bd974b77bee37b95899a92ad
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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