Trimethyl orthovalerate → 2-(1-n-Butyl-1-methoxymethyleneamino)-thiophene-3-carboxylicacid propylamide

HRID 650931Notes

Reaction equation

HRID 650931 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:11]=[CH:10][S:9][C:8]=1[NH2:12])=[O:6])[CH2:2][CH3:3].[C:13](OC)(OC)([O:18][CH3:19])[CH2:14][CH2:15][CH2:16][CH3:17]>CO>[CH2:1]([NH:4][C:5]([C:7]1[CH:11]=[CH:10][S:9][C:8]=1[N:12]=[C:13]([CH2:14][CH2:15][CH2:16][CH3:17])[O:18][CH3:19])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 117886752-amino-N-propylthiophene-3-carboxamide

Product 1

HCID 539289552-(1-n-Butyl-1-methoxymethyleneamino)-thiophene-3-carboxylicacid propylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

In a destillation apparatus, a mixture of 1.84 g of 2-aminothiophene-3-carboxylic-acid propylamide and 2.43 g of trimethyl orthovalerate is heated for 2 hours at 130° C. Methanol, which arises during the reaction is directly distilled out of the reaction flask. After cooling, the crude product is purified by column chromatography (eluant:hexane/ethylacetate=1:2). Yield:1.9 g pure 2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide; m.p. 68-70° C.

Workup

  1. distillationis directly distilled out of the reaction flask
  2. temperatureAfter cooling
  3. customthe crude product is purified by column chromatography (eluant:hexane/ethylacetate=1:2)

Sources & evidence

ORD record
ord-8a79abdb323e46cabeab776212a780a5
Source dataset
uspto-grants-2001_08
Patent number
US06277858B1

Reaction notes

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