Acetyl chloride → 3-Nitroacetanilide

HRID 236236Notes

Reaction equation

HRID 236236 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl>[CH3:19][C:18]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 74233-NitroanilineHCID 8471Triethylamine

Product 1

HCID 312063-Nitroacetanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 13.8 g of 3-nitroaniline and 20 mL of triethylamine in 200 mL methylene chloride was cooled to 0° C. under a nitrogen atmosphere and treated with 10.2 g of acetyl chloride, added in a dropwise manner. The reaction mixture was allowed to warm to room temperature overnight. Removal of the volatiles in vacuo gave a crude yellow solid which was washed with 5% aqueous hydrochloric acid, water and was then dried. The yield of 3-nitroacetanilide was 17.4 g as a light yellow solid, m.p. 147°-149° C.; NMR (CDCl3 /DMSO-d6): δ 2.1 (3H, br s), 7.5 (1H, t, J=9 Hz), 8.0 (2H, br t), 8.6 (1H, br s) 10.1 (1H, br s); IR(KBr): 1675, 1550, 1525, 1350 cm-1.

Workup

  1. additionadded in a dropwise manner
  2. temperatureto warm to room temperature overnight
  3. customRemoval of the volatiles in vacuo
  4. customgave a crude yellow solid which
  5. washwas washed with 5% aqueous hydrochloric acid, water
  6. customwas then dried

Sources & evidence

ORD record
ord-89a852176eae4d168432c3e38564098d
Source dataset
uspto-grants-1987_02
Patent number
US04643759

Reaction notes

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