O-Ethyl carbamothioate → HCID 21502757, compound

HRID 1288536Notes

Reaction equation

HRID 1288536 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 14682382HCID 14682382, compound

Product 1

HCID 21502757HCID 21502757, compound

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-84c86614c6324ed980c3fe7ed2012302
Source dataset
uspto-grants-1976_10
Patent number
US03988444

Reaction notes

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