Diethyl Ether → HCID 19829884, compound

HRID 1493600Notes

Reaction equation

HRID 1493600 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C(=O)(O)[O-:11].[Na+].[CH3:15][CH2:16][O:17][CH2:18]C>ClCC(OC)=O>[CH3:18][O:17][C:16](=[O:11])[CH2:15][NH:5][C:4]1[CH:6]=[CH:7][C:8]([F:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 774693,4-DifluoroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 19829884HCID 19829884, compound

Reagents, catalysts & solvents 1

HCID 7295Methyl chloroacetateSolvent

Procedure

A suspension of 3,4-difluoroaniline (15.0 g) and sodium bicarbonate (19.5 g) in methyl chloroacetate (15.2 ml) was stirred at 80°-90° under nitrogen for 16 h. The cooled reaction mixture was poured into ether (100 ml) and filtered. The filtrate was washed with 2N aqueous hydrochloric acid (100 ml), dried and concentrated to give a solid (16.5 g) which was recrystallised from dichloromethane (20 ml) and n-hexane (40 ml) to give the title compound (9.21 g), m.p. 71°-73°.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with 2N aqueous hydrochloric acid (100 ml)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd17d2a92ffe4d67906560d7f64bb242
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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