Benzene, 1-chloro-3-isocyanato- → HCID 13544859, compound

HRID 1863022Notes

Reaction equation

HRID 1863022 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Cl:30][C:31]1[CH:32]=[C:33]([N:37]=[C:38]=[O:39])[CH:34]=[CH:35][CH:36]=1>C(Cl)Cl>[Cl:30][C:31]1[CH:32]=[C:33]([NH:37][C:38]([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[CH:26]=[CH:27][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)[CH2:21][CH2:22]2)=[O:39])[CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 13544859HCID 13544859, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (2.0 g, 0.005 mol) in 15 ml of methylene chloride is added a solution of m-chlorophenyl isocyanate in 10 ml of methylene chloride at 0° C. under nitrogen. The resulting suspension is stirred for 1 hour at room temperature. The above mixture is then filtered and the white solid residue is washed with more methylene chloride and dried. This is recrystallized from methanol/methylene chloride to give 2.5 g (90%) of white crystalline 1-[[(3-chlorophenyl)amino]carbonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine of melting point 266°-268° C.

Workup

  1. filtrationThe above mixture is then filtered
  2. washthe white solid residue is washed with more methylene chloride
  3. customdried
  4. customThis is recrystallized from methanol/methylene chloride

Sources & evidence

ORD record
ord-e575fcc780c340b4a060c96d5d0d0c34
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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