Methyl chloroformate → HCID 126509864, compound

HRID 1499995Notes

Reaction equation

HRID 1499995 reaction equation
[CH3:1][S:2]([C:5]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:6]=1[C:7]([NH:9][C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)=[O:8])(=[O:4])=[O:3].[H-].[Na+].Cl[C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])O.[Na+]>C1COCC1.O>[CH3:1][S:2]([C:5]1[CH:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[CH:16][C:6]=1[C:7]([N:9]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:27](=[O:28])[O:29][CH3:30])=[O:8])(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 71813020HCID 71813020, compound

Product 1

HCID 126509864HCID 126509864, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 175 mg (0.5 mmol) of 2-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide in 4 ml of THF (abs.) under protective gas at 0° C. are added 14 mg (0.55 mmol) of sodium hydride (95%). After stirring for 10 min, 46 μl (0.6 mmol) of methyl chloroformate are added at 0° C. The reaction mixture is stirred at RT for 1 h. Subsequently, the reaction mixture is adjusted to pH 7 with an aqueous sat. sodium hydrogencarbonate solution, and 10 ml of water are added. Then the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. Yield: 231 mg (57%)

Workup

  1. stirringThe reaction mixture is stirred at RT for 1 h
  2. additionare added
  3. extractionThen the mixture is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37cf793ab9bc4373aaf3c0d0c9f4cba2
Source dataset
uspto-grants-2015_12
Patent number
US09204650B2

Reaction notes

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