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

HRID 1197144Notes

Reaction equation

HRID 1197144 reaction equation
[CH2:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH3:2].[CH3:8][CH:9]1OC(C)OC(C)O1.[CH:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].P(=O)(O)(O)O>O.C(O)=O>[CH2:8]([C:5]1[S:4][C:3]([CH:1]([NH:26][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=2)[CH3:2])=[CH:7][CH:6]=1)[CH3:9]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 133882-EthylthiopheneHCID 31264ParaldehydeHCID 69277Benzamide, 4-(1-methylethyl)-

Product 1

HCID 19897912N-[1-(5-ethyl-2-thienyl)ethyl]-4-isopropylbenzamideYield 83.1%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

2-Ethylthiophene (5.60 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) and subjected to a silica gel column chromatography (eluent: chloroform) to obtain the entitled compound (2.5 g) as a viscous yellow brown liquid. Yield: 83.1%.

Workup

  1. extractionThe mixture was extracted with chloroform (50 ml)

Sources & evidence

ORD record
ord-a441a09e722440f79ceeea2de2abc2b0
Source dataset
uspto-grants-1992_05
Patent number
US05117000

Reaction notes

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