Potassium Carbonate → HCID 18999619, compound

HRID 274114Notes

Reaction equation

HRID 274114 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].Br[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>CN(C=O)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([S:26]([NH:25][CH:21]2[CH2:22][CH2:23][CH2:24][CH:20]2[O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 18999620HCID 18999620, compound

Product 1

HCID 18999619HCID 18999619, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 2.5 g (15 mmoles) of methyl 4-hydroxybenzeneacetate, 4 g (30 mmoles) of K2CO3 and 30 ml of DMF is heated to 80° C. A solution of 5 g (14.8 mmoles) of N-(2-bromocyclopentyl)-4-chlorobenzenesulfonamide as in example 5a is added dropwise thereto, in 50 ml of DMF. The mixture is stirred 5 h at 80° C. After cooling, the solid which is present is filtered and rinsed with ethyl acetate. The filtrate which is diluted with water is extracted with ethyl acetate. The organic phase is washed with water, dried over Na2SO4 and concentrated under reduced pressure. The residue which is purified by chromatography on a column of silica (eluant:hexane-ethyl acetate 1/1) gives 6.2 g (yield=99.5%) of a yellow liquid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid which is present is filtered
  3. washrinsed with ethyl acetate
  4. additionThe filtrate which is diluted with water
  5. extractionis extracted with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue which is purified by chromatography on a column of silica (eluant:hexane-ethyl acetate 1/1)

Sources & evidence

ORD record
ord-21af874c7f4345e49f14df8e7786514b
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

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