Methanesulfonyl chloride → HCID 19347999, compound

HRID 1637193Notes

Reaction equation

HRID 1637193 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([S:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)=[O:17])=[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:13][C:12]=2[CH:31]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([S:16]([C:15]2[C:11]3[CH:10]=[CH:9][C:8]([CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:31][C:12]=3[S:13][C:14]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:17])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 19347997HCID 19347997, compound

Product 1

HCID 19347999HCID 19347999, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.043 ml, 0.55 mmol) was added to a stirred solution of ethyl 6-(hydroxymethyl)-3-[(3-methoxyphenyl)sulfinyl]benzo[b]thiophene-2-carboxylate (Preparation 17, 195 mg, 0.5 mmol) and N-ethyl-N,N-diisopropylamine (0.1 ml, 0.55 mmol) in dichloromethane (3 ml) at 0° C. After 3 hours the solution was washed twice with water, dried (magnesium sulfate), and the solvent removed under reduced pressure. The residue was crystallised from diethyl ether to give the title compound as a colourless solid (155 mg).

Workup

  1. washAfter 3 hours the solution was washed twice with water
  2. dry with materialdried (magnesium sulfate)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was crystallised from diethyl ether

Sources & evidence

ORD record
ord-dcdb52a804d142059094f8e1d224c8a9
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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