2,2-Difluoroethanamine → HCID 86666469, compound

HRID 1189657Notes

Reaction equation

HRID 1189657 reaction equation
[F:1][CH:2]([F:5])[CH2:3][NH2:4].[Cl:6][C:7]1[CH:15]=[C:14](F)[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]>C1COCC1>[Cl:6][C:7]1[CH:15]=[C:14]([NH:4][CH2:3][CH:2]([F:5])[F:1])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 1362742,2-DifluoroethanamineHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 86666469HCID 86666469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2,2-difluoroethylamine (1.65 mL, 23 mmol) and THF (50 mL) is added to a mixture of 2-chloro-4-fluoro-5-nitro-benzoic acid (5.00 g, 22 mmol), TEA (6.33 mL, 45 mmol) and 50 mL THF. The mixture is stirred overnight at rt and 30 h at 60° C., concentrated and diluted with water. The resulting precipitate is collected by filtration, washed with water and dried. Yield: 3.3 g (61%); HPLC Rt=1.14 min (method A). MS m/z: 281 [M+H]+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-746a54d4f72847078ae87b1b372995dd
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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