Hydrochloric Acid → HCID 68516982, compound

HRID 503028Notes

Reaction equation

HRID 503028 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH:22]S(C4C=CC=CC=4)(=O)=O)(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:32]([F:35])([F:34])[F:33])[CH:9]=2)=[CH:4][CH:3]=1.[Cl:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41].Cl>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH:22][C:40](=[O:41])[CH2:39][CH2:38][CH2:37][Cl:36])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:32]([F:34])([F:35])[F:33])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 68517974HCID 68517974, compound

Product 1

HCID 68516982HCID 68516982, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

At a solution of N-[4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenylsulfonyl]benzensulfonamide (1 g, 2.262 mmol) in pyridine (50 ml) cooled at 0° C., 4-chlorobutyrylchloride was added dropwise (0.294 ml), the solution was maintained under stirring for 10 minutes at 0° C., the temperature was then raised to room temperature and the solution was maintained under stirring for 2 hours. Then HCl was added (50 ml, 0.1 N) and the mixture was extracted with CH2Cl2. The combined organic phases were washed with water, dried and the solvent was evaporated at reduced pressure. The crude compound as purified by chromatography on a silica gel column with n-hehan/ethyl acetate 8/2 as eluent to give 0.400 mg of product 4A.

Workup

  1. temperaturethe solution was maintained
  2. temperaturethe temperature was then raised to room temperature
  3. temperaturethe solution was maintained
  4. stirringunder stirring for 2 hours
  5. extractionthe mixture was extracted with CH2Cl2
  6. washThe combined organic phases were washed with water
  7. customdried
  8. customthe solvent was evaporated at reduced pressure
  9. customThe crude compound as purified by chromatography on a silica gel column with n-hehan/ethyl acetate 8/2 as eluent

Sources & evidence

ORD record
ord-252ef45a4d5e47fba7ee8ac015850722
Source dataset
uspto-grants-2010_08
Patent number
US07776902B2

Reaction notes

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