Chlorophenyl isocyanate → HCID 86758513, compound

HRID 1280579Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]([NH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1)=[O:23]

Participants

Reactant 2

HCID 76833Chlorophenyl isocyanate

HCID 86585162HCID 86585162, compound

Product 1

HCID 86758513HCID 86758513, compoundYield 94.8%

Conditions

Temperature: 102.5 °C

Procedure

To a suspension of ethyl 4-amino-2-methylthiopyrimidine-5-carboxylate (1215 g, 5.7 moles) in 2600 mL xylenes heated at 100-105° C. was added (956.5 g, 6.23 moles 2-chlorophenylisocyanate so as to maintain the temperature at 100° C. The temperature of the reaction mixture was raised to 120° C. and stirred for 14 hours. Heating was stopped and slow cooling to 110° C. was begun. When crystallization began, slow addition of 5256 mL ethyl acetate completed the crystallization. The mixture was cooled to 20° C. and filtered. The cake was washed with ethyl acetate and was placed in a vacuum oven and dried for 10-12 hours at 60° to 80° C. to give 1895 g (90.7%)of ethyl 4-{[(2-chlorophenyl)amino]carbonylamino}-2-methylthiopyrimidine-5-carboxylate, m.p.172.3-172.6° C.

Workup

temperatureto maintain the temperature at 100° C
temperatureThe temperature of the reaction mixture was raised to 120° C.
temperatureHeating
temperatureslow cooling to 110° C.
customWhen crystallization
additionslow addition of 5256 mL ethyl acetate
customthe crystallization
temperatureThe mixture was cooled to 20° C.
filtrationfiltered
washThe cake was washed with ethyl acetate
customdried for 10-12 hours at 60° to 80° C.

Sources & evidence

ORD record: ord-025f4ec53be7420fa196507e1fa9879b
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451804B1

Reaction notes

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