Dicyclohexylamine → 1-Phenyl-4-cyano-5-(dicyclohexylaminosulfonylureido)pyrazole

HRID 375702

Reaction equation

HRID 375702 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]1([N:14]2[C:18]([NH2:19])=[C:17]([C:20]#[N:21])[CH:16]=[N:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH:29]1([NH:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.O>[C:8]1([N:14]2[C:18]([NH:19][C:6]([NH:5][S:2]([N:35]([CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)[CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:4])=[O:3])=[O:7])=[C:17]([C:20]#[N:21])[CH:16]=[N:15]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 7582DicyclohexylamineHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 792565-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 189937111-Phenyl-4-cyano-5-(dicyclohexylaminosulfonylureido)pyrazoleYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4.4 ml (50 mmol) of chlorosulfonyl isocyanate were added to a solution of 9.2 g (50 mmol) of 1-phenyl-4-cyano-5-aminopyrazole in 100 ml of methylene chloride. Stirring was carried out for 30 minutes at about 20° C., after which a solution of 7.5 ml (60 mmol) of triethylamine and 10 ml (50 mmol) of dicyclohexylamine in 50 ml of methylene chloride was slowly added dropwise. After the end of the addition, stirring was continued for a further hour and hydrolysis was then carried out with 200 ml of water. The organic phase was separated off and was worked up in a conventional manner to give the product. Yield: 87%.

Workup

  1. additionAfter the end of the addition
  2. stirringstirring
  3. waitwas continued for a further hour
  4. customhydrolysis
  5. customThe organic phase was separated off
  6. customto give the product

Sources & evidence

ORD record
ord-892ac24930964938b65e8098dccb8a46
Source dataset
uspto-grants-1996_01
Patent number
US05486618

Linked notes

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