Dimethylformamide → HCID 54508018, compound

HRID 1602510Notes

Reaction equation

HRID 1602510 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]=[CH:18][C:19]1[CH:47]=[CH:46][C:22]([C:23]([NH:25][C:26]2[CH:31]=[C:30]([CH2:32][CH2:33][CH2:34][S:35]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH:29]=[CH:28][C:27]=2[OH:45])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]=[CH:18][C:19]1[CH:47]=[CH:46][C:22]([C:23]([NH:25][C:26]2[CH:31]=[C:30]([CH2:32][CH2:33][CH2:34][S:35]([C:38]3[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=3)(=[O:37])=[O:36])[CH:29]=[CH:28][C:27]=2[O:45][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 53752128HCID 53752128, compound

Product 1

HCID 54508018HCID 54508018, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, ethyl bromoacetate (87 mg, 0.52 mmol) was added dropwise to a mixture of 4-[2-(2-benzothiazolyl)vinyl]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-hydroxybenzanilide (307 mg, 0.52 mmol), potassium carbonate (145 mg, 1.05 mmol) and dimethylformamide (10 ml), and the resulting reaction solution was stirred at room temperature for 12 hours. Water was added to the reaction solution and the product formed was extracted with ethyl acetate. The resulting extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=4:1) to give ethyl 2-[4-[2-(2-benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (219 mg, 0.32 mmol, 62%) as colorless solid.

Workup

  1. temperatureUnder ice-cooling
  2. customthe resulting reaction solution
  3. customthe product formed
  4. extractionwas extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed with water and brine in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c45d15a5c0c34457a0b10bf4cf5be80f
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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