2,6-Difluoroaniline → Benzamide, N-[[(2,6-difluorophenyl)amino]carbonyl]-2,6-dimethoxy-

HRID 1262464Notes

Reaction equation

HRID 1262464 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[CH3:10][O:11][C:12]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:13]=1[C:14]([N:16]=[C:17]=[O:18])=[O:15]>C(Cl)Cl>[CH3:24][O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:12]([O:11][CH3:10])[C:13]=1[C:14]([NH:16][C:17]([NH:4][C:3]1[C:2]([F:1])=[CH:8][CH:7]=[CH:6][C:5]=1[F:9])=[O:18])=[O:15]

Participants

4

Reactant 2

HCID 796472,6-DifluoroanilineHCID 133219942,6-Dimethoxybenzoyl isocyanate

Product 1

HCID 163518Benzamide, N-[[(2,6-difluorophenyl)amino]carbonyl]-2,6-dimethoxy-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 60 g. portion of 2,6-difluoroaniline was dissolved in 1500 ml. methylene chloride and cooled to 10° C. Under a nitrogen atmosphere, 90 g. of 2,6-dimethoxybenzoylisocyanate in 200 ml. methylene chloride was added dropwise. The mixture was allowed to stir at 25° C. for three hours. The solid was collected and washed with water. The filtrate was evaporated to dryness, and 150 ml. diethyl ether and 150 ml. ethanol were added. The solid was again collected. Yield 89.0 g. (60%).

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customThe filtrate was evaporated to dryness, and 150 ml
  4. additionethanol were added
  5. customThe solid was again collected

Sources & evidence

ORD record
ord-eba46eb16ae14d7594e644762324890e
Source dataset
uspto-grants-1984_06
Patent number
US04452631

Reaction notes

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