Methyl chloroformate → HCID 19417497, compound

HRID 865005Notes

Reaction equation

HRID 865005 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O:10].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]([OH:36])=[C:23]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[CH3:35])[C:24](=[O:26])[N:25]=2)=[CH:16][CH:15]=1>C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:21][C:22]([O:36][C:9]([O:11][CH3:12])=[O:10])=[C:23]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[CH3:35])[C:24](=[O:26])[N:25]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178424614HCID 178424614, compound

Product 1

HCID 19417497HCID 19417497, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

1.0 g (10 mmol) of triethylamine and then 0.94 g (10 mmol) of methyl chloroformate in 10 ml of ethyl acetate are added dropwise at 0° C. to 3.4 g (10 mmol) of 2-(4-fluorophenyl)-6-hydroxy-5-(2,4,6-trimethyl-phenyl)-1,3-thiazin-4-one in 50 ml of ethyl acetate. The mixture is stirred for 8 hours at 20° C. and filtered, the organic phase is washed using half-concentrated sodium chloride elusion and dried over sodium sulphate, and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel (35 to 70 μm) using toluene/acetone (20:1 parts by volume). 3.1 g of 2-(4-fluorophenyl)-6-methoxycarbonyloxy-5-(2,4,6-trimethylphenyl)-1,3-thiazin-4-one are obtained (yield: 78% of theory). M.p.=129° to 131° C.

Workup

  1. filtrationfiltered
  2. washthe organic phase is washed
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is chromatographed on silica gel (35 to 70 μm)

Sources & evidence

ORD record
ord-b7b25fae364945d6936dce539458e075
Source dataset
uspto-grants-1996_10
Patent number
US05565450

Reaction notes

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