Dimethylformamide → HCID 15734807, compound

HRID 1030208Notes

Reaction equation

HRID 1030208 reaction equation
Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:8]1[CH:7]2[CH:2]1[C:3]([CH3:20])([CH3:19])[O:4][C:5]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])=[CH:9][C:6]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67791553HCID 67791553, compound

Product 1

HCID 15734807HCID 15734807, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of trans-3-bromo-3,4-dihydro-4-hydroxy-N,N,2,2-tetramethyl-2H-1-benzopyran-6-sulfonamide (19.2 g), potassium carbonate (15 g) and dimethylformamide (153 ml) was stirred at room temperature for 24 hours and followed by at 35° C. for 48 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated to give 3,4-dihydro-3,4-epoxy-N,N,2,2-tetramethyl-2H-1-benzopyran-6-sulfonamide (4.7 g).

Workup

  1. waitfollowed by at 35° C. for 48 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-28a21ec4b4c04d17aa67f0726057430b
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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