Hydrochloric Acid → HCID 69102861, compound

HRID 2220399Notes

Reaction equation

HRID 2220399 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([S:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29].C1CCN2C(=NCCC2)CC1.Cl>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:7])=[C:4]([S:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 24824646HCID 24824646, compound

Product 1

HCID 69102861HCID 69102861, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-(isopropylthio)benzoic acid (47.90 g) in N,N-dimethylformamide (480 ml) was added 1,1′-carbonyldiimidazole (31.00 g) and stirred for 30 minutes at room temperature under nitrogen atmosphere. To the mixture were added methanesulfonamide (18.17 g) and 1,8-diazabicyclo[5.4.0]-7-undecene (39.10 ml) and then stirred at room temperature overnight. The reaction mixture was poured into hydrochloric acid aqueous solution (1N, 2 l) and extracted with ethyl acetate (2 l). The separated organic layer was washed with water (2 l) and brine (2 l), dried over magnesium sulfate and concentrated in vacuo. Then the residue was dried to give 4-bromo-2-(isopropylthio)-N-(methylsulfonyl)benzamide (60.00 g) as a white solid.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with ethyl acetate (2 l)
  3. washThe separated organic layer was washed with water (2 l) and brine (2 l)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThen the residue was dried

Sources & evidence

ORD record
ord-a843415d6d034f0f87e64e7a73c3f597
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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