Potassium Carbonate → HCID 22627946, compound

HRID 278582Notes

Reaction equation

HRID 278582 reaction equation
Cl[CH2:2][S:3]([N:6]1[CH2:11][CH2:10][N:9]([CH:12]=[O:13])[CH2:8][CH2:7]1)(=[O:5])=[O:4].[Cl:14][C:15]1[CH:22]=[C:19]([CH:20]=O)[C:18]([OH:23])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[O:23][C:2]([S:3]([N:6]3[CH2:11][CH2:10][N:9]([CH:12]=[O:13])[CH2:8][CH2:7]3)(=[O:5])=[O:4])=[CH:20][C:19]=2[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 22627936HCID 22627936, compound

Product 1

HCID 22627946HCID 22627946, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(chloromethanesulfonyl)-4-formylpiperazine (2.26 g), 5-chlorosalicylaldehyde (1.56 g) and potassium carbonate (1.38 g) in DMF (30 ml) was stirred at 100° C. for 48 hours. The reaction solution was concentrated, and to the residue was added ethyl acetate. The organic layer was washed with water and brine, dried, concentrated and purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of 1-(5-chlorobenzofurane-2-sulfonyl)-4-formylpiperazine (406 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue was added ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-68f03bec345643a6b5b1c0cd36319337
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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