Ethyl Acetate → HCID 89760871, compound

HRID 1479161Notes

Reaction equation

HRID 1479161 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].C([O-])(O)=O.[Na+].Cl.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([CH3:29])[CH2:27][CH:26]2[NH2:28])=[CH:21][CH:20]=1.CCOC(C)=O>ClCCl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@@:25]2([CH3:29])[CH2:27][C@H:26]2[NH:28][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 874382,6-Difluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 131736574HCID 131736574, compound

Product 1

HCID 89760871HCID 89760871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-difluorobenzoyl chloride (156 mg, 0.881 mmol) was added to a rapidly stirred mixture of NaHCO3 (1 M aq., 4 ml) and a solution of racemic (1R,2R)-2-(4-chlorophenyl)-2-methyl-cyclopropanamine hydrochloride (172 mg, 0.735 mmol) in dichloromethane (4.5 ml). After stirring for 30 minutes EtOAc was added, the organic phase was separated, washed with brine, dried over MgSO4, and the solvent evaporated to give 241 mg, 100%) of racemic N-[(1R,2R)-2-(4-chlorophenyl)-2-methyl-cyclopropyl]-2,6-difluoro-benzamide. M.p. 140-142° C.

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-6a1b4d58c56749739ed3dadf1f4ffd55
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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