Potassium Carbonate → Carbamic acid, (4-amino-2-methyl-5-nitrophenyl)-, 2-chloroethyl ester

HRID 2417751Notes

Reaction equation

HRID 2417751 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.Cl[C:26]([O:28][CH2:29][CH2:30][Cl:31])=[O:27]>O>[CH3:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH:4][C:26](=[O:27])[O:28][CH2:29][CH2:30][Cl:31]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123052-Chloroethyl chloroformateHCID 312751,4-DioxaneHCID 54879441,4-Benzenediamine, 2-methyl-5-nitro-

Product 1

HCID 14774569Carbamic acid, (4-amino-2-methyl-5-nitrophenyl)-, 2-chloroethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.6 mol (100 g) of 2-methyl-4-amino-5-nitroaniline and 0.36 mol (50 g) of potassium carbonate are introduced into 500 ml of dioxane to which 145 ml of water have been added. The mixture is heated to 90° C., whilst stirring, and 0.6 mol (86 g) of chloroethyl chloroformate is then added gradually in the course of 10 minutes. When the addition has ended, the heating is maintained for 10 minutes at 90° C., the reaction medium is cooled to 15° C. and the expected product is then filtered off. After washing with a small amount of dioxane and then with water and alcohol, the product is recrystallised from dioxane and then dried in vacuo. It melts at 192° C.

Workup

  1. additionhave been added
  2. additionWhen the addition
  3. temperaturethe heating is maintained for 10 minutes at 90° C.
  4. temperaturethe reaction medium is cooled to 15° C.
  5. filtrationthe expected product is then filtered off
  6. washAfter washing with a small amount of dioxane
  7. customwith water and alcohol, the product is recrystallised from dioxane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-155f7dab50934d108351b6932f910518
Source dataset
uspto-grants-1984_09
Patent number
US04470826

Reaction notes

Loading…