Triethylamine → N'-(4-((3,6-dichloro-2-pyridinyl)methoxy)phenyl)-N-methoxy-N-methyl urea

HRID 436686

Reaction equation

C(N(CC)CC)C.Cl.[CH3:9][O:10][NH:11][CH3:12].[Cl:13][C:14]1[C:15]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=2)=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=1>N1C=CC=CC=1>[Cl:13][C:14]1[C:15]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:31])[N:11]([O:10][CH3:9])[CH3:12])=[CH:25][CH:24]=2)=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Triethylamine (4.55 grams; 0.045 mole) was added to a solution of O,N-dimethylhydroxylamine hydrochloride (4.1 grams; 0.042 mole) in 40 ml. of dry pyridine. 3,6-dichloro-2-((4-isocyanatophenoxy)methyl)pyridine (12.4 grams; 0.042 mole) was added thereto and the resulting mixture heated for 20 minutes at about 60° C. The reaction mixture was then mixed with ice and the resulting precipitate recovered by filtration and recrystallized from a benzenehexane (90:10) mixture. As a result of such operations, the desired N'-(4-((3,6-dichloro-2-pyridinyl)methoxy)phenyl)-N-methoxy-N-methyl urea compound was recovered as a crystalline solid having a melting point of 152° -153.5° C.

Workup

additionThe reaction mixture was then mixed with ice
filtrationthe resulting precipitate recovered by filtration
customrecrystallized from a benzenehexane (90:10) mixture
customAs a result of such operations
customthe desired N'-(4-((3,6-dichloro-2-pyridinyl)methoxy)phenyl)-N-methoxy-N-methyl urea compound was recovered as a crystalline solid

Sources & evidence

ORD record: ord-89915b24e7e84d4ca7e58507a2f843f3
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028092

Linked notes

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