Phosphoric Acid → N-[1-(3-bromo-2-thienyl)ethyl]-4-isopropylbenzamide

HRID 1197143Notes

Reaction equation

HRID 1197143 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][CH:8]1OC(C)OC(C)O1.[CH:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=1)([CH3:18])[CH3:17].P(=O)(O)(O)O>O.C(O)=O>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]([NH:25][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([CH:16]([CH3:18])[CH3:17])=[CH:20][CH:21]=1)[CH3:8]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 133833-BromothiopheneHCID 31264ParaldehydeHCID 69277Benzamide, 4-(1-methylethyl)-

Product 1

HCID 19897911N-[1-(3-bromo-2-thienyl)ethyl]-4-isopropylbenzamideYield 17%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

3-Bromothiophene (8.15 g, 0.05 mol), paraldehyde (2.20 g, 0.017 mol) and 4-isopropylbenzamide (1.63 g, 0.01 mol) were added to a mixture of formic acid (6 ml) and 85% phosphoric acid (3 ml) and stirred at a room temperature for four hours. Water (50 ml) was added to the reaction mixture. The mixture was extracted with chloroform (50 ml), subjected to a silica gel column chromatography (eluent: chloroform) and recrystallized from chloroform/petroleum benzine (1:2) to obtain the entitled compound (0.6 g) as a colorless plate-shape crystal. Yield: 17.0%. Melting point: 133° C.

Workup

  1. extractionThe mixture was extracted with chloroform (50 ml)
  2. customrecrystallized from chloroform/petroleum benzine (1:2)

Sources & evidence

ORD record
ord-8cad702cee3f4bffbf519ecb8a9ea6de
Source dataset
uspto-grants-1992_05
Patent number
US05117000

Reaction notes

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