Water → HCID 22133219, compound

HRID 1856836Notes

Reaction equation

HRID 1856836 reaction equation
[C:1]([O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[Cl:13])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:22][C:23]1S[CH:25]=[CH:26][C:27]=1[C:28](Cl)=[O:29].[OH2:31]>CCOCC.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([NH:12][C:28]([C:27]2[CH:26]=[CH:25][O:31][C:23]=2[CH3:22])=[O:29])[CH:9]=[CH:8][C:7]=1[Cl:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 22133221HCID 22133221, compoundHCID 22414448HCID 22414448, compound

Product 1

HCID 22133219HCID 22133219, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 22.8 g of the 5-amino-2-chlorobenzoyl acetate from Step 3 above and 17.2 ml of triethylamine in 118 ml ether was prepared and then added dropwise to a second solution of 16.6 g 2-methyl-3-thiophenecarboxylic acid chloride in 118 ml ether at 0° C. to 10° C. and the resultant mixture was stirred at room temperature overnight. 100 ml of water and 100 ml of ethyl acetate were then added to the mixture, the organic phase separated, washed with 2N hydrochloric acid and water, dried over magnesium sulfate, and the solvents removed in vacuo, to produce 29.87 g of N-(3-acetoxymethyl-4-chlorophenyl)-2-methyl-3-furancarboxamide as a beige solid.

Workup

  1. customthe organic phase separated
  2. washwashed with 2N hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-f609cacdd4f04b258d908fad82e03470
Source dataset
uspto-grants-2000_11
Patent number
US06143780

Reaction notes

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