2,6-Difluorobenzoyl isocyanate → N-(2,6-difluorobenzoyl)-N'-[4-(alpha-cyclopropyl-4-chlorobenzyloxy)phenyl]urea

HRID 1285561Notes

Reaction equation

HRID 1285561 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[CH:14]1([CH:17]([O:25][C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15]1>C(#N)C>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([NH:6][C:7]([NH:30][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH:17]([CH:14]2[CH2:15][CH2:16]2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:32][CH:31]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 202495884-[(4-Chlorophenyl)(cyclopropyl)methoxy]aniline

Product 1

HCID 20249576N-(2,6-difluorobenzoyl)-N'-[4-(alpha-cyclopropyl-4-chlorobenzyloxy)phenyl]urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,57 g of 2,6-difluorobenzoylisocyanate was added to a solution of 3,35 g 4-(α-cyclopropyl-4-chlorobenzyloxy)aniline in 30 ml of dry acetonitrile while stirring. After stirring for 1 hour at room temperature the formed precipitate was sucked off, washed with acetonitrile, and dried. The desired product was obtained in a yield of 2.90 g; melting point 185°-188° C. The structure was confirmed by means of CMR.

Workup

  1. stirringAfter stirring for 1 hour at room temperature the formed precipitate
  2. washwashed with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-3420ce6dbb5c4b78a77b911bdea63e38
Source dataset
uspto-grants-1986_01
Patent number
US04567295

Reaction notes

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