Carbamate → HCID 21251132、化合物

HRID 1532146ノート

反応式

HRID 1532146 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][C:9](=O)N(C)C.C[O-].[Na+].C(=O)([O-])N.C[O-].[Na+].CO.[Br:31][CH2:32][CH2:33]CBr>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:33][CH2:32][Br:31]

参加物

7

反応物 5

HCID 276CarbamateHCID 80011,3-DibromopropaneHCID 10942334Sodium MethoxideHCID 15840683HCID 15840683、化合物HCID 23694274Sodium methanolate methanol

生成物 1

HCID 21251132HCID 21251132、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

実験手順

To a solution of methyl 3-chloro-4-dimethylcarbamoylthiophenylacetate (8.5 g, 0.0295 mol) in methanol (30 mL) was added 25% NaOMe in methanol (7.0 mL, 0.034 mol). The reaction was heated to reflux for 2 h. TLC analysis shows residual starting carbamate. Additional NaOMe/MeOH (1.0 mL) was added and the mixture stirred an additional 30 min at reflux. After cooling to ambient temperature, the thiolate solution was added dropwise to a solution of 1,3-dibromopropane (12 mL, 0.12 mol) in methanol (30 mL). The resulting solution was refluxed for 3 h then cooled to ambient temperature, After standing overnight, the reaction was quenched by pouring into ice water. After adjusting to pH1 with conc. HCl, the aqueous solution was extracted with EtOAc (0.2 L then 2×0.1 L). The combined organics were washed with water, brine, dried over anhyd. MgSO4, filtered, and concentrated. The residue was chromatographed over silica gel with 10% of ethyl acetate in hexane to afford the title compound.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. temperatureat reflux
  4. temperatureThe resulting solution was refluxed for 3 h
  5. temperaturethen cooled to ambient temperature
  6. waitAfter standing overnight
  7. customthe reaction was quenched
  8. additionby pouring into ice water
  9. extractionthe aqueous solution was extracted with EtOAc (0.2 L
  10. washThe combined organics were washed with water, brine
  11. customdried over anhyd
  12. filtrationMgSO4, filtered
  13. concentrationconcentrated
  14. customThe residue was chromatographed over silica gel with 10% of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-98c30212f3d144e198e0f6af38cc851d
出典データセット
uspto-grants-2001_03
特許番号
US06200998B1

反応ノート

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