4-Chlorobenzenesulfonamide → HCID 178513456, compound

HRID 1727386Notes

Reaction equation

HRID 1727386 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Al](C)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:27][CH:26]([C:28]#[N:29])[N:25]=[C:24]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[CH:19][CH:18]=1.CO.O>C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:27][CH:26]([C:28]([NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])=[NH:29])[N:25]=[C:24]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 668244-ChlorobenzenesulfonamideHCID 16682925TrimethylaluminumHCID 21082125HCID 21082125, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 178513456HCID 178513456, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

Part A: To a suspension of 4-chlorobenzenesulfonamide (0.45 gram, 0.00236 mol) in benzene (5 ml) is dropwise added trimethylaluminum (1.2 ml of a 2N solution in toluene, 0.0024 mol) to give a clear solution which is stirred at room temperature for 1 hour. 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-4,5-dihydro-1H-imidazole-4-carbonitrile (0.55 gram, 0.00157 mol) is added and the resulting mixture is heated at 90° C. for 16 hours. After cooling to room temperature a mixture of methanol/water (8/2 (v/v)) is slowly added, the solids are removed by filtration and washed with chloroform (50 ml). The filtrate is concentrated in vacuo. The residue is triturated with n-pentane and twice recrystallised from methanol to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-N-[(4-chlorophenyl)sulfonyl]-4,5-dihydro-1H-imidazole-4-carboxamidine (0.435 gram, 51% yield). Melting point: 165-166° C. 1H-NMR (200 MHz, CDCl3): δ 4.11-4.35 (m, 2H), 4.94 (dd, J=12 and 10 Hz, 1H), 6.63 (br d, J=8 Hz, 2H), 7.12 (br d, J=8 Hz, 2H), 7.22-7.52 (m, 6H), 7.90 (br d, J=8 Hz, 2H), 8.10-8.20 (m, 1H).

Workup

  1. customto give a clear solution which
  2. temperaturethe resulting mixture is heated at 90° C. for 16 hours
  3. temperatureAfter cooling to room temperature
  4. additionis slowly added
  5. customthe solids are removed by filtration
  6. washwashed with chloroform (50 ml)
  7. concentrationThe filtrate is concentrated in vacuo
  8. customThe residue is triturated with n-pentane
  9. customtwice recrystallised from methanol

Sources & evidence

ORD record
ord-f30bd22bc235421ea3eacb26914b029d
Source dataset
uspto-grants-2009_02
Patent number
US07495108B2

Reaction notes

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