Ammonium Hydroxide → HCID 57475858, compound

HRID 1049290Notes

Reaction equation

HRID 1049290 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.C(Cl)(=O)C(Cl)=O.[NH4+:17].[OH-]>C(Cl)Cl.CN(C=O)C.C1COCC1>[F:1][C:2]([F:10])([F:9])[C:3]1([C:6]([NH2:17])=[O:7])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acid

Product 1

HCID 57475858HCID 57475858, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(trifluoromethyl)cyclopropane-1-carboxylic acid (0.5 g, 3.24 mmol) in DCM (5 mL) was treated with oxalyl chloride (0.355 mL, 4.06 mmol) and 1 drop of DMF, stirred for 1 h at RT, added drop-wise to a solution of NH4OH (˜15M, 5 mL, ˜75 mmol) in THF (5 mL) and stirred at RT overnight. The solids were removed via filtration through diatomaceous earth and rinsed well with 4:1 DCM/THF. The filtrate was saturated with solid NaCl, extracted with 4:1 DCM/THF (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 1-(trifluoromethyl)cyclopropanecarboxamide (440 mg, 89%). 1H NMR (400 MHz, DMSO-d6): δ 7.31 (s, 1H), 7.15 (s, 1H), 1.29-1.24 (m, 2H), 1.19-1.15 (m, 2H).

Workup

  1. stirringstirred at RT overnight
  2. customThe solids were removed via filtration through diatomaceous earth
  3. washrinsed well with 4:1 DCM/THF
  4. extractionextracted with 4:1 DCM/THF (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1e9e13cc40a74fa09a12dd884aafa5a8
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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