Water → HCID 18321885, compound

HRID 613627Notes

Reaction equation

HRID 613627 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][OH:19])[C:12]=2[Cl:20])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[C:1]([NH:4][CH2:5][C:6]1[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][O:19][S:29]([CH3:28])(=[O:31])=[O:30])[C:12]=2[Cl:20])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18321895HCID 18321895, compound

Product 1

HCID 18321885HCID 18321885, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-acetamidomethyl-1-(2,4-dichloro-3-hydroxymethylphenyl)pyrrole (51 mg) and triethylamine (19.8 mg) in dichloromethane (2 ml) was added methanesulfonyl chloride (20.5 mg) under nitrogen atmosphere in ice-methanol bath, and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with water, saturated sodium bicarbonate solution and brine, dried over magensium sulfate and evaporated in vacuo to give 2-acetamidomethyl-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole (64 mg) as oil.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magensium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6ea1c2965422450f8466265d99df4f0d
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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