Phenylacetaldehyde → HCID 54726812, compound

HRID 974200Notes

Reaction equation

HRID 974200 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[OH:13][C:14]1[C:15]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:16]=2[S:17][C:18]=1[C:19]([NH2:21])=[O:20].[C:30]1([CH2:36][CH:37]=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:39]1(C)C=CC=CC=1>>[OH:13][C:14]1[C:15]2[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][C:16]=2[S:17][C:18]=1[C:19]([N:21]([CH:37]=[CH:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:39]=[CH:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 4

HCID 998PhenylacetaldehydeHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 54680210HCID 54680210, compound

Product 1

HCID 54726812HCID 54726812, compoundYield 21%

Procedure

p-Toluenesulfonic acid monohydrate (55 mg) was added to a mixture of 3-hydroxy-5-trifluoromethylbenzo[b]thiophene-2-carboxamide (1.1 g, 4.4 mmol) and phenylacetaldehyde (1.0 g, 8.8 mmol) in toluene (25 ml). The reaction mixture was heated to reflux for 0.5 hours utilizing a Dean-Stark trap to collect the water formed during reaction. The solution was cooled, filtered and the filtrate concentrated. The residue was subjected to column chromatography on silica gel (E. Merck #7734), eluting with 1% acetic acid in 5:1 hexane/ether. Fractions containing the product were concentrated and the residue was recrystallized from cyclohexane to give 0.31 g (21%) of 3-hydroxy-N,N-di-(2'-phenylethenyl)-5-trifluoromethylbenzo[b]thiophene-2-carboxamide, m.p. 165°-167° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 0.5 hours
  3. customto collect the water
  4. customformed during reaction
  5. temperatureThe solution was cooled
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated
  8. washeluting with 1% acetic acid in 5:1 hexane/ether
  9. additionFractions containing the product
  10. concentrationwere concentrated
  11. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-3a8db4e9776745309be92e649068ac8a
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

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