Methyl chloroformate → HCID 67164907, compound

HRID 552619Notes

Reaction equation

HRID 552619 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]4[N:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[O:19])=[C:16]([CH3:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:35]([O:37][CH3:38])=[O:36]>[H-].[Na+].O1CCCC1>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:30]([F:31])([F:33])[F:32])[O:13][N:12]=[C:11]([C:14]3[CH:28]=[CH:27][C:17]([C:18]([N:20]([C:21]4[N:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:35](=[O:36])[O:37][CH3:38])=[O:19])=[C:16]([CH3:29])[CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 44629046HCID 44629046, compound

Product 1

HCID 67164907HCID 67164907, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 24758Sodium hydrideSolvent

Procedure

In 0.02 g of 55% oily sodium hydride suspended in 3 mL of tetrahydrofuran, a solution of 0.17 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyrimidinyl)benzoic acid amide synthesized similarly to Step 5 of Synthetic Example 1 in 3 mL of tetrahydrofuran was added dropwise. After the completion of the addition dropwise, it was continued to stir at the same temperature for 10 minutes, then 0.05 g of methyl chloroformate was added, and continued to stir at the same temperature for 1 hour. After the completion of the reaction, the reaction mixture was poured in 10 mL of ice water, extracted with ethyl acetate (10 mL×2), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate to obtain 0.11 g of the aimed product as colorless resinous substance.

Workup

  1. additionwas added dropwise
  2. additionAfter the completion of the addition dropwise
  3. stirringto stir at the same temperature for 1 hour
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (10 mL×2)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-fdb4ed5996ff46da8d9de3fb495eb7a9
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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