Methyl Isocyanate → 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl methylcarbamate

HRID 1722970Notes

Reaction equation

HRID 1722970 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[C:11]([OH:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[C:8]([F:26])[CH:7]=1>C(N(CC)CC)C.C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:4])[O:12][C:11]1[CH:10]=[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[N:15]([CH3:24])[C:14]2=[O:25])[C:8]([F:26])=[CH:7][C:6]=1[Cl:5]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 541768922-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl methylcarbamate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.51 g of methyl isocyanate and subsequently one drop of triethylamine are added at room temperature while stirring to a solution of 2.00 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 20 ml of methylene chloride. The reaction mixture is stirred for one hour and evaporated to dryness under reduced pressure. The residue is purified by chromatography on a silica gel column using diethyl ether-n-hexane (2:1) as the eluent. There is obtained 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl methylcarbamate, 1H-NMR (CDCl3, 400 MHz): 7.33 ppm (d,1H), 7.24 ppm (d,1H), 6.34 ppm (s,1H), 5.21 ppm (q,1H), 3.54 ppm (d,3H), 2.88 ppm (d,3H).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-3d8c48e103114bcfb3499cb3c81dc84f
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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