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

HRID 980418Notes

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:25][CH2:26][CH2:27][O:28][C:29](Cl)=[O:30]>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:29](=[O:30])[O:28][CH2:27][CH2:26][Cl:25]

Participants

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 brought to 90° C., while stirring, and 0.6 mol (86 g) of chloroethylchloroformate is added a little at a time, in the course of 10 minutes. When the addition has ended, heating at 90° C. is continued for 10 minutes and the reaction mixture is cooled to 15° C. and the expected product is filtered off with suction. After being washed with a little dioxane and then with water and alcohol, the product is recrystallised from dioxane and then dried in vacuo. It has a melting point of 192° C.

Workup

additionhave been added
customis brought to 90° C.
customin the course of 10 minutes
additionWhen the addition
temperaturethe reaction mixture is cooled to 15° C.
filtrationthe expected product is filtered off with suction
washAfter being washed with a little dioxane
customwith water and alcohol, the product is recrystallised from dioxane
customdried in vacuo

Sources & evidence

ORD record: ord-7265f95b274042d98f6baa66fcdd38b2
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04637821

Reaction notes

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