Hydrochloric Acid → HCID 15615501, compound

HRID 1194312Notes

Reaction equation

HRID 1194312 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[Cl:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=C(S(C)(=O)=O)[N:12]=1.Cl>O1CCCC1.O>[NH:3]([C:1]1[N:12]=[C:11]([Cl:10])[CH:16]=[C:15]([O:17][CH3:18])[N:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7671FormanilideHCID 137292254-Chloro-2-(methanesulfonyl)-6-methoxypyrimidine

Product 1

HCID 15615501HCID 15615501, compoundYield 114.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.8 g of formanilide was dissolved in 50 ml of tetrahydrofuran, and 0.4 g of sodium hydride from which the oily matter had been removed before hand with n-hexane was slowly added to the resulting solution at 10° to 20° C. while cooling with ice water. To the suspension thus obtained was added 3.3 g of 4-chloro-2-methanesulfonyl-6-methoxypyrimidine, and the mixture was stirred for 1 hour at room temperature. Then, 15 ml of 4N hydrochloric acid was added, and reaction was effected for 1 hour under reflux. The reaction liquid was poured in water, extracted with ether, and the ether layer was washed with water, dried over magnesium sulfate, and then the ether was stripped by concentration. The residual crystals were recrystallized from n-hexane, and 4.0 g of 2-anilino-4-chloro-6-methoxypyrimidine was obtained (yield 87%). Melting point: 101°-103° C.

Workup

  1. custom0.4 g of sodium hydride from which the oily matter had been removed before hand with n-hexane
  2. additionwas slowly added to the resulting solution at 10° to 20° C.
  3. temperaturewhile cooling with ice water
  4. customTo the suspension thus obtained
  5. customreaction
  6. waitwas effected for 1 hour
  7. temperatureunder reflux
  8. customThe reaction liquid
  9. extractionextracted with ether
  10. washthe ether layer was washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationthe ether was stripped by concentration
  13. customThe residual crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-980d832fa79b4bb79e3ceb9b3eb2e60c
Source dataset
uspto-grants-1989_03
Patent number
US04814338

Reaction notes

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