Sulfuric Acid → Cyclafuramid

HRID 597257

Reaction equation

HRID 597257 reaction equation
[C:1]([O:4][CH:5]([CH3:8])[CH:6]=O)(=O)[CH3:2].[CH:9]1([NH:15][C:16](=[O:21])[CH2:17]C(C)=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.OS(O)(=O)=O>C1(C)C=CC=CC=1>[CH:9]1([NH:15][C:16]([C:17]2[CH:6]=[C:5]([CH3:8])[O:4][C:1]=2[CH3:2])=[O:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 70805N-CyclohexylacetoacetamideHCID 907282-(Acetyloxy)propanal

Product 1

HCID 93178Cyclafuramid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

24 parts (by weight) of α-acetoxypropionaldehyde is stirred with 36.6 parts of acetoacetic cyclohexylamide and 1 part of concentrated H2SO4 in 100 parts of toluene for 3 hours at 50° C. After the mixture has been cooled to room temperature it is washed with sodium hydrogen carbonate. The organic phase is dried with Na2SO4 and concentrated to dryness. There is obtained 41 parts of 2,5-dimethylfuran-3-carboxylic cyclohexylamide having a melting point of 111° to 113° C. After recrystallization from cyclohexane the compound melts at 114° to 115° C.

Workup

  1. washis washed with sodium hydrogen carbonate
  2. dry with materialThe organic phase is dried with Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-14610cf6caa1447a8c7e66842238ed42
Source dataset
uspto-grants-1977_03
Patent number
US04013684

Linked notes

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