Methyl chloroformate → HCID 67164907, compound

HRID 1187950Notes

Reaction equation

HRID 1187950 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-94a419756a91477aa060ddc09619ca21
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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