4-Nitroaniline → 2-(2-chloroethoxy)-N-(4-nitrophenyl)acetamide

HRID 2246805Notes

Reaction equation

HRID 2246805 reaction equation
Cl[C:2]1([Cl:8])[CH2:7][O:6][CH2:5][CH2:4][O:3]1.[N+:9]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)([O-:11])=[O:10]>>[Cl:8][CH2:2][CH2:7][O:6][CH2:5][C:4]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=1)=[O:3]

Participants

3

Reactant 2

HCID 74754-NitroanilineHCID 124243252,2-Dichloro-1,4-dioxane

Product 1

HCID 116158572-(2-chloroethoxy)-N-(4-nitrophenyl)acetamide

Conditions

Temperature
80 °C

Procedure

1.53 g of a mixture of 2-chlorodioxene and 2,2-dichlorodioxane (molar ratio 1:1) are added to 1.00 g (7.24 mmol) of 4-nitroaniline, and the mixture is heated to 80° C. with stirring. A solid brown mass forms within one hour and becomes liquid again and crystallises within the following 12 hours. The crude product is recrystallised from ethanol with addition of water, giving 1.80 g of 2-(2-chloroethoxy)-N-(4-nitrophenyl)acetamide (“A1”) as yellowish crystals, m.p. 101-102° C. 1H-NMR (d6-DMSO): δ=3.82 (m; 4H), 4.23 (s; 2H), 7.91 (d, J=9 Hz, 2H), 8.23 (d, J=9 Hz, 2H), 10.34 (s, 1H).

Workup

  1. customcrystallises within the following 12 hours
  2. customThe crude product is recrystallised from ethanol with addition of water

Sources & evidence

ORD record
ord-f977f05c02f14736b1bdb0c0309a60a6
Source dataset
uspto-grants-2010_03
Patent number
US07687624B2

Reaction notes

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