O-Ethyl carbamothioate → 4-Carbomethoxy-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one

HRID 1580090Notes

Reaction equation

HRID 1580090 reaction equation
[C:1](=[S:6])([O:3]CC)[NH2:2].Br[CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([O:16][CH3:17])=[O:15])[C:9]1=O>O1CCOCC1>[C:14]([CH:10]1[C:9]2[NH:2][C:1](=[O:3])[S:6][C:8]=2[CH2:13][CH2:12][CH2:11]1)([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 3032339O-Ethyl carbamothioateHCID 14682382Methyl 3-bromo-2-oxo-cyclohexanecarboxylate

Product 1

HCID 215027574-Carbomethoxy-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 10.5 g of ethyl thiocarbamate, 25.9 g of methyl 3-bromo-2-oxo-cyclohexanecarboxylate and 200 ml of dioxane was refluxed for 16 hours and was then distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 1-1 cyclohexane-ethyl acetate mixture to obtain 4-carbomethoxy-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one melting at 95°C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. distillationwas then distilled to dryness under reduced pressure
  3. customThe residue was chromatographed over silica gel
  4. washwas eluted with a 1-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-eea7f310c24642399a4094d224ef75df
Source dataset
uspto-grants-1976_01
Patent number
US03932433

Reaction notes

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