Ethanol → HCID 12393363, compound

HRID 514743Notes

Reaction equation

HRID 514743 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][CH2:13][OH:14].C([Cl:18])(=O)C>>[ClH:18].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8](=[NH:9])[O:14][CH2:13][CH3:12])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 120904-Nitrobenzonitrile

Product 1

HCID 12393363HCID 12393363, compoundYield 63.6%

Procedure

To a solution of 4-nitrobenzonitrile (27 g, 182 mmol) in EtOH (128 ml, 2187 mmol) under nitrogen was added acetyl chloride (104 ml, 1458 mmol) dropwise at 0° C. over 1 h, and the reaction was warmed to room temperature. The flask was sealed and the reaction was stirred for 56 h. The resulting precipitate (4-nitrobenzamide) was collected by filtration, and the filtrate was treated with diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether and air dried to give the title compound (26.7 g, 58%): mp 198-200° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.37-8.30 (m, 2H), 8.21-8.13 (m, 2H), 7.35 (s, 1H), 7.22 (s, 1H), 7.09 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H); EIMS m/z 193 [M+].

Workup

  1. customThe flask was sealed
  2. filtrationThe resulting precipitate (4-nitrobenzamide) was collected by filtration
  3. additionthe filtrate was treated with diethyl ether
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with diethyl ether and air
  6. customdried

Sources & evidence

ORD record
ord-be976087152046a3b04eee5e4ac8b54c
Source dataset
uspto-grants-2015_08
Patent number
US09108932B2

Reaction notes

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