Methanesulfonyl chloride → HCID 17952495, compound

HRID 1828189Notes

Reaction equation

HRID 1828189 reaction equation
[CH:1]1([N:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14]O)=[CH:13][C:8]=3[N:7]([CH3:16])[C:6]2=[O:17])[CH2:4][CH2:3][CH2:2]1.CS([Cl:22])(=O)=O>ClCCl.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>[Cl:22][CH2:14][C:12]1[CH:11]=[CH:10][C:9]2[N:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[C:6](=[O:17])[N:7]([CH3:16])[C:8]=2[CH:13]=1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 17952496HCID 17952496, compound

Product 1

HCID 17952495HCID 17952495, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

1-Cyclobutyl-5-hydroxymethyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (13.79 g, 59.4 mmol) was diluted with dichloromethane (300 mL) and triethylamine (12.4 mL). The reaction was cooled to 0° C. and methanesulfonyl chloride (6.9 mL, 89.1 mmol) was added. The mixture was stirred for 1 hour at 0° C. then was diluted with saturated sodium bicarbonate and extraced into dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The resulting oil was filtered through silica gel using ethyl acetate containing 1% triethylamine as eluent to give 11.92 g of 5-Chloromethyl-1-cyclobutyl-3-methyl-1,3-dihydro-benzoimidazol-2-one.

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. concentrationconcentrated
  3. filtrationThe resulting oil was filtered through silica gel

Sources & evidence

ORD record
ord-8ef8c35e96754e58bdd8326a36d816f5
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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