Formic Acid → N-[1-(5-bromo-2-thienyl)ethyl]-4-isopropylbenzamide

HRID 1197142Notes

Reaction equation

HRID 1197142 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=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].C(O)=O>O>[Br:1][C:2]1[S:3][C:4]([CH:7]([NH:25][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([CH:16]([CH3:18])[CH3:17])=[CH:20][CH:21]=2)[CH3:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 138512-BromothiopheneHCID 31264ParaldehydeHCID 69277Benzamide, 4-(1-methylethyl)-

Product 1

HCID 19897913N-[1-(5-bromo-2-thienyl)ethyl]-4-isopropylbenzamideYield 8.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-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 formic acid (10 ml) and stirred at a room temperature for three 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 (0.3 g) as a colorless needle-shape crystal. Yield: 8.5%. Melting point: 108° C.

Workup

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

Sources & evidence

ORD record
ord-b671a7c18c7146be82b58bf7f918eed7
Source dataset
uspto-grants-1992_05
Patent number
US05117000

Reaction notes

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