2,6-Difluorobenzoyl isocyanate → Flucycloxuron

HRID 465158

Reaction equation

HRID 465158 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([C:17](=[N:25][O:26][CH2:27][C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15]1>C(OCC)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:32][C:31]1[CH:33]=[CH:34][C:28]([CH2:27][O:26][N:25]=[C:17]([CH:14]2[CH2:16][CH2:15]2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:29][CH:30]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 54230357(4-Chlorophenyl)cyclopropylmethanone O-[(4-aminophenyl)methyl]oxime

Product 1

HCID 86309Flucycloxuron

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

36.6 g of 2,6-difluorobenzoylisocyanate in 50 ml of dry diethyl ether were added to a solution of 59.0 g 4-(α-cyclopropyl-4-chlorobenzylideneaminooxymethyl)aniline in 700 ml of dry diethylether with external cooling at 0°-10° C. After stirring for 3 hours at 0°-10° C. the formed precipitate was sucked off, washed with diethyl ether, and dried. The product obtained in a yield of 76.0 g was chromatographed over silica, chloroform being used as an eluent. The desired product was isolated in a yield of 60,7 g having a purity of at least 95% (PMR). The product obtained had a melting range of 145°-175° C. and comprised the syn- and anti-form in approximately equal amounts. In another experiment the desired product was obtained as a mixture of the syn- and anti-form in a ratio of 85:15; melting point 187°-191° C.

Workup

  1. temperaturewith external cooling at 0°-10° C
  2. washwashed with diethyl ether
  3. customdried
  4. customThe product obtained in a yield of 76.0 g
  5. customwas chromatographed over silica, chloroform being

Sources & evidence

ORD record
ord-a5f6fd491a2445cd85b97772a6b968ac
Source dataset
uspto-grants-1985_10
Patent number
US04550202

Linked notes

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