Triethylamine → 3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

HRID 394438Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([O:15]C(OC)=O)=[CH:13][C:12]([N:20]=[C:21]=[O:22])=[C:11]([F:23])[CH:10]=1.CNC(NC)=[S:27].[CH:30]1[N:34]=[CH:33][N:32]([C:35](N2C=NC=C2)=[O:36])[CH:31]=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[C:14]([OH:15])=[CH:13][C:12]([N:20]2[C:21](=[O:22])[N:34]([CH3:30])[C:33](=[S:27])[N:32]([CH3:31])[C:35]2=[O:36])=[C:11]([F:23])[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3 ml of triethylamine and then a solution of 22.4 g (91.2 mmol) of 4-chloro-2-fluoro-5-(methoxycarbonyloxy)phenyl isocyanate in 100 ml of toluene were added dropwise at approximately 20° C. to a solution of 9.5 g (91.2 mmol) of N,N′-dimethylthiourea in 20 ml of toluene. After addition of 29.6 g (182.5 mmol) of carbodiimidazole, the mixture was heated for 3 hours at 80° C. The reaction mixture was stirred overnight at approximately 20° C., then washed three times with water and finally concentrated under reduced pressure. The crude product was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=10:1). Yield: 18.1 g (63%); m.p.: 242-246° C.

Workup

washwashed three times with water
concentrationfinally concentrated under reduced pressure
customThe crude product was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=10:1)

Sources & evidence

ORD record: ord-90af2d4d430c4942919cdb81700c9595
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602825B1

Reaction notes

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