Hydrochloric Acid → HCID 59641737, compound

HRID 2250333Notes

Reaction equation

HRID 2250333 reaction equation
[NH:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:6]=[C:5]([C:21]([F:24])([F:23])[F:22])[N:4]=1)[NH2:2].[C:25](Cl)(=[O:27])[CH3:26].Cl>N1C=CC=CC=1>[C:9]1([C:8]2[C:3]([NH:1][NH:2][C:25](=[O:27])[CH3:26])=[N:4][C:5]([C:21]([F:24])([F:23])[F:22])=[N:6][C:7]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 100195084-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 59641737HCID 59641737, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.7 g, 2.1 mmol) (synthesized according to the procedure described in example 21) in pyridine (10 ml) was added acetylchloride (0.17 g, 2.2 mmol) dropwise at 20° C. under stirring for 10 minutes. After 30 minutes of stirring, the reaction mixture was poured onto ice-water mixture, acidified to pH 4 using hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to furnish the title compound (0.2 g, 25.4%, HPLC purity 99.4%), mp: 113-116° C.

Workup

  1. stirringAfter 30 minutes of stirring
  2. additionthe reaction mixture was poured onto ice-water mixture
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6c7076cd986e48b1a1c1eed702c89aa2
Source dataset
uspto-grants-2008_01
Patent number
US07317014B2

Reaction notes

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