Benzyl mercaptan → 2-(Benzylsulfanyl)-5-bromopyrimidine

HRID 905220Notes

Reaction equation

HRID 905220 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1>CC[O-].[Na+]>[CH2:1]([S:8][C:10]1[N:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7509Benzyl mercaptanHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 204757122-(Benzylsulfanyl)-5-bromopyrimidineYield 81%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

Benzyl thiol (22 mmol) was added to 0.146 M ethanolic NaOEt (150 ml) at room temperature followed by 2-chloro-5-bromopyrimidine (20 mmol). The mixture was stirred at room temperature for 70 min, heated under reflux for 40 min, the solvent evaporated off at reduced pressure, the residue extracted with chloroform (100 ml), the chloroform solution washed with 2 M NaOH, and the dried (MgSO4) solution evaporated; yield 81%, m.p. 68°-69° C. (dil. MeOH). 1H NMR (CDCl3): δ4.36 (CH2), 7.26 (Ph), 8.50. (H-4, H-6).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 min
  3. customthe solvent evaporated off at reduced pressure
  4. extractionthe residue extracted with chloroform (100 ml)
  5. washthe chloroform solution washed with 2 M NaOH
  6. dry with materialthe dried (MgSO4) solution
  7. customevaporated

Sources & evidence

ORD record
ord-f5eec3961e484c66a0c6179918ee6957
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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