Water → HCID 18551155, compound

HRID 1266435Notes

Reaction equation

HRID 1266435 reaction equation
[CH2:1]([NH:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[Br:13])[CH:2]=[CH2:3].[CH2:15]([CH2:19][C:20](=O)[CH3:21])[C:16]([CH3:18])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(OCC)(=O)C>[CH2:1]([NH:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20]([CH3:21])=[CH:19][CH:15]=[C:16]2[CH3:18])=[CH:8][C:7]=1[Br:13])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 18551198HCID 18551198, compound

Product 1

HCID 18551155HCID 18551155, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11 g of 4-amino-2-bromobenzoic acid-allylamide, 5.2 ml of acetonylacetone and 200 mg of 4-toluenesulfonic acid are refluxed for 1.5 hours with a water separator. Then, the solution is diluted with ethyl acetate, washed with 1N hydrochloric acid and then with potassium carbonate solution, dried (Na2SO4) and concentrated by evaporation. The residue is crystallized with hexane. 13.4 g of N-allyl-2-bromo-4-(2,5-dimethylpyrrol-1-yl)-benzamide, melting point 136-138° C., is obtained.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialwith potassium carbonate solution, dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customThe residue is crystallized with hexane

Sources & evidence

ORD record
ord-0931807e9de14e33bfb2aaa4bad4f255
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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