Sodium Chloride → 2-(4-Nitrophenylthio)pyrimidine

HRID 1074206Notes

Reaction equation

HRID 1074206 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[OH-].[K+].[Cl-].[Na+]>O.CS(C)=O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([S:1][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 178418793HCID 178418793, compound

Product 1

HCID 881572-(4-Nitrophenylthio)pyrimidineYield 43%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1.12 g (10 mmoles) of 2-mercaptopyrimidine, 1.4 (10 mmoles) of 1-fluoro-4-nitrobenzene, 0.5 of potassium hydroxide and 10 ml of dimethylsulfoxide were heated at 120°-130° C. for 6 hours and then cooled. After pouring into a mixture of ice, water and sodium chloride the mixture was allowed to stand for 30 minutes and then filtered. The solid was washed with water, air dried and chromatographed on silica gel using ethyl acetate/hexane (1:1 by volume) as the eluent. The fractions containing the product were combined and concentrated to give 1 g (43%) of the product as yellow rods, mp 103°-104° C.

Workup

  1. temperaturewere heated at 120°-130° C. for 6 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid was washed with water, air
  5. customdried
  6. customchromatographed on silica gel
  7. additionThe fractions containing the product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c56284a6f72c42cd94129b5466279754
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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