Dimethylamine → HCID 10245550, compound

HRID 1607668Notes

Reaction equation

HRID 1607668 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8](Cl)=[O:9].[CH3:22][NH:23][CH3:24]>O1CCCC1.O>[CH3:22][N:23]([CH3:24])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:5]([O:4][C:3]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:2]=2[F:1])[CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 10448313HCID 10448313, compound

Product 1

HCID 10245550HCID 10245550, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 3-(2,4-difluorophenoxy)-4-nitrobenzoyl chloride (2.2 g) in tetrahydrofuran (8 ml) was added dropwise to a stirred solution of dimethylamine (50% in water; 2 ml) in water (10 ml) at 5° C. The mixture was stirred for 30 minutes at 5° C. and for 1 hour at room temperature. The mixture was concentrated and extracted with chloroform. The extract was washed with water, dried, and concentrated under reduced pressure. The residue (2.4 g) was solidified with a mixture of hexane and ethanol to give pale brown powder of N,N-dimethyl-3-(2,4-difluorophenoxy)-4-nitrobenzamide (2.0 g).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue (2.4 g) was solidified with a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-741bf426048a493d935eec3ba474166d
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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