2-Fluoroaniline → 4-Methyl-n-(2,2,2-trichloro-1-{[(2-fluoroanilino)carbonyl]amino}ethyl)benzamide

HRID 479497Notes

Reaction equation

HRID 479497 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10]1[CH:26]=[CH:25][C:13]([C:14]([NH:16][CH:17]([N:22]=[C:23]=[O:24])[C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])=[CH:12][CH:11]=1>C1COCC1>[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][CH:17]([NH:22][C:23]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])=[O:24])[C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 187707404-methyl-N-(2,2,2-trichloro-1-isocyanatoethyl)benzamide

Product 1

HCID 187706244-Methyl-n-(2,2,2-trichloro-1-{[(2-fluoroanilino)carbonyl]amino}ethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-fluoroaniline (132 mg, 1.40 mmol) in THF (8 mL) at ambient temperature was treated with a solution of Example 43A (386 mg, 1.26 mmol) in THF (1.5 mL). The reaction mixture was stirred for 2 hours and concentrated to a nominal volume. The white solids which precipitated from solution were collected by filtration and washed with diethyl ether. Recrystallization from 25% ethyl acetate/hexanes provided the desired product as a white solid.

Workup

  1. concentrationconcentrated to a nominal volume
  2. customThe white solids which precipitated from solution
  3. filtrationwere collected by filtration
  4. washwashed with diethyl ether
  5. customRecrystallization from 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e9be08bc14e042ddafecf5d04b8ddbec
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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