Potassium Carbonate → HCID 20098389, compound

HRID 1165239Notes

Reaction equation

HRID 1165239 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([OH:23])=[C:9]([CH:22]=1)[C:10]([NH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)=[O:11])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:30]([CH:32]1[O:34][CH2:33]1)Br>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:23][CH2:30][CH:32]2[CH2:33][O:34]2)=[C:9]([CH:22]=1)[C:10]([NH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430Epibromohydrin2×HCID 20098380HCID 20098380, compound

Product 1

HCID 20098389HCID 20098389, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.5 g of the product of Step C, 150 ml of acetone, 1.5 g of potassium carbonate and 9 ml of epibromohydrin was refluxed for 2 hours and after the addition of another 9 ml of epibromohydrin, the mixture was refluxed for 20 hours and was filtered. The filtrate was washed with acetone and evaporated to dryness under reduced pressure at 50° C. The residue was taken up in ether and was filtered. The product was dried at 80° C. to obtain 3.4 g of 5-acetylamino-2-[(2-oxiranyl)-methoxy]-N-(1H-indol-4-yl)-benzamide melting at 230° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 20 hours
  3. filtrationwas filtered
  4. washThe filtrate was washed with acetone
  5. customevaporated to dryness under reduced pressure at 50° C
  6. filtrationwas filtered
  7. customThe product was dried at 80° C.

Sources & evidence

ORD record
ord-ac848479f5f94215b43a605580f820a1
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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