Potassium Carbonate → HCID 57517767, compound

HRID 2040433Notes

Reaction equation

HRID 2040433 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2([OH:24])[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[CH3:23].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[S:35](Cl)(=[O:37])=[O:36].S(Cl)(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:35]([C:28]1[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=1[O:26][CH3:25])(=[O:37])=[O:36])[C:12](=[O:17])[C:11]2([OH:24])[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[CH3:23]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 23665647Potassium tert-butoxide2×HCID 57517766HCID 57517766, compound

Product 1

HCID 57517767HCID 57517767, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (1.21 g, 10.8 mmol) was added to an ice-cold solution of the intermediate from Step A (3.00 g, 10.8 mmol) in DMF (30 ml), and the mixture was stirred at 0° C. for 30 min. After addition of 2,4-dimethoxy-benzenesulfonyl chloride (2.5 g, 10.8 mmol), the reaction mixture was left to stir at 0° C. for 1 hour. Further addition of 0.2 equivalent each of potassium tert-butoxide and sulfonyl chloride led to no further advance in the reaction according to thin-layer chromatography. The reaction mixture was stirred into dilute potassium carbonate solution, and the resulting precipitate was filtered off. The precipitate was taken up in ethyl acetate, and the extract was washed with saturated brine and dried over magnesium sulfate. Purification by chromatography (silica gel, gradient 30% to 50% ethyl acetate in heptane) and recrystallization from diethyl ether resulted in 0.96 g of the desired product.

Workup

  1. waitthe reaction mixture was left
  2. stirringto stir at 0° C. for 1 hour
  3. filtrationthe resulting precipitate was filtered off
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification
  7. customby chromatography (silica gel, gradient 30% to 50% ethyl acetate in heptane) and recrystallization from diethyl ether

Sources & evidence

ORD record
ord-0c1d586ce0774cebaa5079f904f7f5e6
Source dataset
uspto-grants-2013_11
Patent number
US08580842B2

Reaction notes

Loading…