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

HRID 1651456ノート

反応式

HRID 1651456 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-51c520f98d0f46a3b1d7cb84c3471d45
出典データセット
uspto-grants-1990_05
特許番号
US04927822

反応ノート

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