Carbon Disulfide → ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate

HRID 977952ノート

反応式

HRID 977952 の反応式
[CH2:1]([NH:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=[S:19])=[S:18].[OH-].[K+].Cl/[CH:23]=[CH:24]\Cl>CS(C)=O.O>[S:18]1[CH:24]=[CH:23][S:19][C:17]1=[C:11]([C:9](=[O:10])[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

7

反応物 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 643833cis-1,2-Dichloroethylene2 回HCID 11379032Ethyl 3-(benzylamino)-3-oxopropanoate

生成物 1

HCID 20204019ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate収率 62.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

実験手順

Ethyl (N-benzylcarbamoyl)acetate (39.00 g) and carbon disulfide (14.03 g) are dissolved in dimethylsulfoxide (390 ml). A solution of potassium hydroxide (21.52 g) in water (39 ml) is added dropwise to the mixture at 20° to 40° C. The mixture is stirred at the same temperature for 30 minutes, and then cis-1,2-dichloroethylene (17.84 g) is added dropwise thereto. The mixture is stirred at 50° C. for 5 hours. Cis-1,2-dichloroethylene (3.24 g) is further added to the mixture 3 hours after the commencement of the reaction. After cooling, the mixture is poured into water, and the aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate=2:1), and then recrystallized from a mixture of n-hexane and ethyl acetate, whereby ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate (33.77 g) is obtained as pale yellow prisms. Yield: 62.8%.

後処理

  1. stirringThe mixture is stirred at 50° C. for 5 hours
  2. customafter the commencement of the reaction
  3. temperatureAfter cooling
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate=2:1)
  10. customrecrystallized from a mixture of n-hexane and ethyl acetate

出典と根拠

ORDレコード
ord-cd08dec0f9c14a658a70021c9cba4417
出典データセット
uspto-grants-1987_05
特許番号
US04663319

反応ノート

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