Methanesulfonyl chloride → HCID 14723693, compound

HRID 1608304Notes

Reaction equation

HRID 1608304 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:21])[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.O>[CH2:29]([N:26]([CH2:27][CH3:28])[CH2:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[CH2:19][N:11]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:3][CH:4]=2)[CH:9]=[N:10]1)[CH3:30]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 14723691HCID 14723691, compound

Product 1

HCID 14723693HCID 14723693, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 8 lg (0.02 mol) of 4-(4-aminophenyl)-N-[3-(diethylamino)propyl]-5-phenyl-1H-pyrazole-1-acetamide of example 46 in 50 mL of pyridine was cooled to 5° C. and 4.6 g (0.04 mol) of methanesulfonyl chloride was added dropwise below 10° C. The reaction was stripped below 60° C. in vacuo, dissolved in about 75 mL of water, treated with excess saturated aqueous sodium bicarbonate, extracted into methylene chloride and stripped. The product was recrystallized from acetonitrile, 7.2 g, mp 179°-180° C.

Workup

  1. customwas stripped below 60° C. in vacuo
  2. extractionextracted into methylene chloride
  3. customThe product was recrystallized from acetonitrile, 7.2 g, mp 179°-180° C.

Sources & evidence

ORD record
ord-d11627ee23c84890b352a49c472c3419
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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