2-Methyl-4-nitroaniline → HCID 11535999, compound

HRID 2246807Notes

Reaction equation

HRID 2246807 reaction equation
Cl[C:2]1(Cl)[CH2:7][O:6][CH2:5][CH2:4][O:3]1.[CH3:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12]>C1COCC1>[N+:17]([C:15]1[CH:14]=[CH:13][C:11]([N:12]2[CH2:2][CH2:7][O:6][CH2:5][C:4]2=[O:3])=[C:10]([CH3:9])[CH:16]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 74412-Methyl-4-nitroanilineHCID 124243252,2-Dichloro-1,4-dioxane

Product 1

HCID 11535999HCID 11535999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1.05 g of a mixture of 2-chlorodioxene and 2,2-dichlorodioxane (molar ratio 1:1) are added to a solution of 1.10 g (7.24 mmol) of 2-methyl-4-nitroaniline in 20 ml of THF, and the mixture is heated to the boil. The solvent is distilled off, and the residue, a brown viscous liquid, is heated at 80° C. for 18 hours. After cooling, the residue is recrystallised from toluene/tert-butyl methyl ether: 1.50 g of 2-(2-chloroethoxy)-N-(2-methyl-4-nitrophenyl)acetamide as yellowish crystals, m.p. 113-114° C. 1H-NMR (d6-DMSO): δ=2.35 (s; 3H), 3.82 (m; 4H), 4.23 (s; 2H), 8.05 (d, J=8 Hz, 1H) 8.09 (dd, J=9 Hz, J=1 Hz, 1H), 8.16 (d, J=1 Hz, 1H), 9.33 (s, 1H).

Workup

  1. temperaturethe mixture is heated to the boil
  2. distillationThe solvent is distilled off
  3. temperatureAfter cooling
  4. customthe residue is recrystallised from toluene/tert-butyl methyl ether

Sources & evidence

ORD record
ord-03d20fd6836a4134b32f5bf29f7c0cac
Source dataset
uspto-grants-2010_03
Patent number
US07687624B2

Reaction notes

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