4-Amino-2,6-dichlorophenol → HCID 14275602, compound

HRID 569728Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].[Cl:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([N:16]=[C:17]=[O:18])=[O:15]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=2[Cl:11])=[O:18])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a reaction flask containing 6.23 grams (35.0 mmol) of 2,6-dichloro-4-aminophenol in 100 milliliters of toluene (heated to a temperature of 100° C. to dissolve the solid) was added with continuous stirring a solution of 7.63 grams (42.0 mmol) of 2-chlorobenzoyl isocyanate dissolved in 25 milliliters of toluene. The resulting exothermic reaction raised the temperature to boiling with the formation of a solid precipitate. Additional amounts of toluene were added to the reaction flask to facilitate stirring until the addition of 2-chlorobenzoyl isocyanate was complete. After cooling to ambient temperature, the solid precipitate was filtered and the residue was washed successively with toluene and hexane and air dried to afford 11.99 grams of 1-(3,5-dichloro-4-hydroxyphenyl)-3-(2-chlorobenzoyl)urea as a light brown solid having a melting point of 220° C.-222° C. Elemental analysis of the light brown solid indicated the following:

Workup

dissolutionto dissolve the solid)
additionwas added
customThe resulting exothermic reaction
temperatureraised the temperature
temperatureAfter cooling to ambient temperature
filtrationthe solid precipitate was filtered
washthe residue was washed successively with toluene and hexane and air
customdried

Sources & evidence

ORD record: ord-94b480fce53c4c4384a7f7a6b5328780
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734404

Reaction notes

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