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

HRID 1980749Notes

Reaction equation

HRID 1980749 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:3]=1.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:3]=[C:4]([NH2:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[NH:8][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 4-methyl-2,5-diamino-nitrobenzene 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 desired 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 desired 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-7469fa6f88254cf9ba59b18eb10ef7d3
Source dataset
uspto-grants-1985_04
Patent number
US04511360

Reaction notes

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