Ethyl Acetate → benzyl 2-cyclohexyl-5,6-dihydro-4H-1,3,4-thiadiazine-5-carboxylate

HRID 1651456Notes

Reaction equation

HRID 1651456 reaction equation
[CH2:1]([O:8][C:9](=[O:13])[C:10](Br)=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]1([C:20]([NH:22][NH2:23])=[S:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.N12CCCC1=NCCC2.C(OCC)(=O)C>C1C=CC=CC=1.CN(C)C=O>[CH:14]1([C:20]2[S:21][CH2:11][CH:10]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:13])[NH:23][N:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 13443472Benzyl 2-bromoprop-2-enoateHCID 14804493Cyclohexane carbothioic acid hydrazide

Product 1

HCID 23051218benzyl 2-cyclohexyl-5,6-dihydro-4H-1,3,4-thiadiazine-5-carboxylateYield 49.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromoprop-2-enoic acid benzyl ester (1.68 g) in dry benzene (10.2 ml) was added to cyclohexane carbothioic acid hydrazide (1.0 g) in dry dimethylformamide (10 ml). The mixture was cooled to 0° and stirred, under an atmosphere of nitrogen, during the gradual addition of 1,5-diazabicyclo[4.3.0]non-5-ene (0.78 g) and then for a further 20 minutes at 0°. Ethyl acetate (100 ml) was added and the mixture was washed with brine and dried over magnesium sulphate The solvent was evaporated under reduced pressure and the resulting oil purified by flash chromatography using 10% ethyl acetate/90% petroleum ether as eluent to yield the sub-title product (1.0 g) as a pink solid.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. washthe mixture was washed with brine
  3. dry with materialdried over magnesium sulphate The solvent
  4. customwas evaporated under reduced pressure
  5. customthe resulting oil purified by flash chromatography

Sources & evidence

ORD record
ord-51c520f98d0f46a3b1d7cb84c3471d45
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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