Ammonium Chloride → 1-(2,2,2-Trifluoro-1-hydroxy-1-methylethyl)cyclopropanesulfonamide

HRID 2369947Notes

Reaction equation

HRID 2369947 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH2:7][CH2:6]1)=[O:4].[CH3:14][Mg]Br.[Cl-].[NH4+]>C1COCC1.C(OCC)C>[F:13][C:2]([F:1])([F:12])[C:3]([C:5]1([S:8]([NH2:11])(=[O:9])=[O:10])[CH2:7][CH2:6]1)([OH:4])[CH3:14]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 867054521-(2,2,2-Trifluoroacetyl)cyclopropanesulfonamideHCID 178418573HCID 178418573, compound

Product 1

HCID 682885021-(2,2,2-Trifluoro-1-hydroxy-1-methylethyl)cyclopropanesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under inert gas, 250 mg of 1-(2,2,2-trifluoroacetyl)cyclopropanesulfonamide were initially charged in 6 ml of THF and then, at a temperature of −78° C., 1.15 ml of a 3.0 N methylmagnesium bromide solution in diethyl ether were added dropwise and the mixture was stirred at constant temperature for 4 hours. The reaction solution was admixed with 5 ml of a saturated aqueous ammonium chloride solution and allowed to come to room temperature while stirring. After adjustment to pH 5 with 2 N aqueous hydrochloric acid, the mixture was extracted with 10 ml of ethyl acetate, and the organic phase was dried over Na2SO4 and concentrated by rotary evaporation. This gave the product (208 mg) with a molecular weight of 233.2 g/mol (C6H10F3NO3S); MS (ESI): m/e=234 (M+H+).

Workup

  1. customto come to room temperature
  2. stirringwhile stirring
  3. extractionAfter adjustment to pH 5 with 2 N aqueous hydrochloric acid, the mixture was extracted with 10 ml of ethyl acetate
  4. dry with materialthe organic phase was dried over Na2SO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-52921795aeeb4eb081ea63c819355095
Source dataset
uspto-grants-2014_04
Patent number
US08710050B2

Reaction notes

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