Heptane → HCID 59520509、化合物

HRID 1162784ノート

反応式

HRID 1162784 の反応式
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][CH2:23][C:24](Cl)=[O:25].CCCCCCC>C1COCC1>[Cl:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:13][CH3:14])=[O:12])=[O:25]

参加物

6

反応物 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 693643-Chloropropionyl chlorideHCID 36564302-amino-N-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

生成物 1

HCID 59520509HCID 59520509、化合物収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Amino-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (2.82 g, 13.41 mmol) was completely dissolved in THF (90 mL). Potassium carbonate (2.22 g, 16.09 mmol) was then added and the reaction stirred for 5 min. 3-chloropropanoyl chloride (2.04 g, 1.536 mL, 16.09 mmol) was added and the reaction mixture stirred at RT for 30 min. THF was removed in vacuo. Water was added and the reaction mixture extracted into EtOAc (×3). The combined EtOAc layers were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. Purification by flash column chromatography-silica gel and elution with 0-60% EtOAc:heptane gave the desired product (1.76 g, 5.87 mmol, 44%).

後処理

  1. stirringthe reaction mixture stirred at RT for 30 min
  2. customTHF was removed in vacuo
  3. additionWater was added
  4. extractionthe reaction mixture extracted into EtOAc (×3)
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification
  10. washby flash column chromatography-silica gel and elution with 0-60% EtOAc

出典と根拠

ORDレコード
ord-36a7562f09bd426d96dfbe29ddeca943
出典データセット
uspto-grants-2010_10
特許番号
US07820707B2

反応ノート

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