Hydrochloric Acid → HCID 46880367, compound

HRID 19761Notes

Reaction equation

HRID 19761 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:15]=2)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.C[CH2:40][N:41](C(C)C)C(C)C>ClCCl.CN.ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:15]=2)=[N:41][CH3:40])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 68692319N-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide

Product 1

HCID 46880367HCID 46880367, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 6329MethylamineSolventHCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

Part B: A stirred mixture of N-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide (2.36 gram, 5 mmol), PCl5 (1.15 g, 5.5 mmol) and chlorobenzene (50 ml) is heated for 90 minutes at 140° C. After cooling the mixture to room temperature the residue is dissolved in dichloromethane and methylamine.HCl (0.34 g, 5 mmol) and DIPEA (1.74 ml, 10 mmol) are successively added. The resulting mixture is stirred for 16 hours at room temperature, twice washed with water, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is further purified by flash chromatography (silica gel, dichloromethane/acetone=99/1 (v/v/), followed by crystallization from diisopropyl ether to give N-[(4-chlorophenyl)sulfonyl]-N′-methyl-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine (0.36 gram, 15% yield). Melting point: 134-144° C. Rf (silica gel, diethyl ether=0.4).

Workup

  1. temperatureAfter cooling the mixture to room temperature the residue
  2. stirringThe resulting mixture is stirred for 16 hours at room temperature
  3. washtwice washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is further purified by flash chromatography (silica gel, dichloromethane/acetone=99/1 (v/v/),
  8. customfollowed by crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-a70826dc398c45cab1e90e7c6d0e73e7
Source dataset
uspto-grants-2010_06
Patent number
US07745476B2

Reaction notes

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