p-Toluenesulfonyl isocyanate → N-[(4-methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine-1-carboxamide

HRID 1863023Notes

Reaction equation

HRID 1863023 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.[C:30]1([CH3:42])[CH:35]=[CH:34][C:33]([S:36]([N:39]=[C:40]=[O:41])(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:42][C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][C:40]([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:41])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 20392887N-[(4-methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine-1-carboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (2 g, 0.005 mol) in 15 ml of methylene chloride under nitrogen is added dropwise a solution of p-tolylsulfonyl-isocyanate in 10 ml of methylene chloride over a period of 10 minutes. After complete addition, the resultant suspension is stirred at room temperature for 1 hour. The white solid is filtered, washed with more methylene chloride, and dried giving 2.6 g (87%) of N-[(4-methylphenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine-1-carboxamide of melting point 253°-255° C. Infrared and mass spectra are consistent with the assigned structure.

Workup

  1. additionAfter complete addition
  2. filtrationThe white solid is filtered
  3. washwashed with more methylene chloride
  4. customdried

Sources & evidence

ORD record
ord-1d185af344d347e7ae1fcdd2f3a67fb5
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

Loading…