Triethylamine → HCID 68468450, compound

HRID 1929291Notes

Reaction equation

HRID 1929291 reaction equation
[CH2:1]([NH:8][NH2:9])C1C=CC=CC=1.C(N(CC)CC)C.[F:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=1[CH2:26][C:27](Cl)=[O:28].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][N:8]([C:27](=[O:28])[CH2:26][C:19]1[C:20]([F:25])=[CH:21][CH:22]=[C:23]([F:24])[C:18]=1[F:17])[NH2:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11157(Phenylmethyl)hydrazineHCID 25517Ammonium ChlorideHCID 83402842HCID 83402842, compound

Product 1

HCID 68468450HCID 68468450, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.22 g (26.4 mmol) of benzyl hydrazine together with 4.4 ml (1.2 eq) of triethylamine and 0.16 g of DMAP (0.05 eq) were initially charged in 50 ml of dichloromethane, and 5.5 g of 2,3,6-trifluorophenylacetyl chloride in 50 ml of dichloromethane were then slowly added dropwise at 0° C. The mixture was then stirred at room temperature overnight, and ammonium chloride solution was added. The organic phase was separated off, dried and concentrated. Purification by column chromatography gave 6.2 g of 2,3,6-trifluorophenylacetic acid 1-methylhydrazide.

Workup

  1. customThe organic phase was separated off
  2. customdried
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-cf0ab86153364cbfb248932c394e1be4
Source dataset
uspto-grants-2012_05
Patent number
US08188008B2

Reaction notes

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