Ethanol → (+)-p-(2-Thenoyl)hydratropic acid alpha-methylbenzylamine

HRID 258901

Reaction equation

HRID 258901 reaction equation
[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][CH:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)C>O>[CH3:19][CH:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5359SuprofenHCID 74081-Phenethylamine

Product 1

HCID 70638167(+)-p-(2-Thenoyl)hydratropic acid alpha-methylbenzylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 20 parts of p-(2-thenoyl)hydratropic acid and 9.3 parts of (-)-α-methylbenzylamine in 200 parts of ethanol are added 50 parts of water. The precipitated salt is filtered off and crystallized from a mixture of ethanol and water (10 : 2 by volume), yielding the crude salt form. This fraction is recrystallized several times till constant rotation, from a mixture of ethanol and water (10 : 2 by volume), to yield (-)-p-(2-thenoyl)hydratropic acid α-methyl-benzylamine; m.p. 170.5° C; [α](1.98% MeOH)= -13.74° .

Workup

  1. filtrationThe precipitated salt is filtered off
  2. customcrystallized from a mixture of ethanol and water (10 : 2 by volume)
  3. customyielding the crude salt form
  4. customThis fraction is recrystallized several times till constant rotation
  5. additionfrom a mixture of ethanol and water (10 : 2 by volume)

Sources & evidence

ORD record
ord-f83e4f81da194e8c9a29418aacf12525
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Linked notes

Loading…