Dimethylformamide → 1-Methylcyclohex-3-ene-1-carboximidic acid

HRID 527021

反応式

HRID 527021 の反応式
[CH3:1][C:2]1([C:8]([OH:10])=O)[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1.S(Cl)(Cl)=O.C[N:16](C=O)C.[OH-].[NH4+]>C(Cl)Cl>[CH3:1][C:2]1([C:8]([NH2:16])=[O:10])[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 860461-Methylcyclohex-3-ene-1-carboxylic acid2 回

生成物 1

HCID 30528401-Methylcyclohex-3-ene-1-carboximidic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-methylcyclohex-3-ene-1-carboxylic acid, 52a, (54.0 g, 385.2 mmol) dissolved in CH2Cl2 (200 mL) was added thionyl chloride (56.2 mL, 770.4 mmol) and 1 mL of DMF. The reaction was warmed to reflux for 3 hrs, then cooled and concentrated in vacuo. The residue was redissolved in 200 mL of CH2Cl2. To the reaction was added ammonium hydroxide (148.2 mL of 13 M solution, 1.9 mol) slowly. The reaction was stirred overnight. The reaction was extracted into CH2Cl2 and water. The organic phase was concentrated in vacuo and purified via flash silica gel chromatography (EtOAc), yielding 25 g of 1-methylcyclohex-3-ene-1-carboxamide.

後処理

  1. temperatureThe reaction was warmed
  2. temperatureto reflux for 3 hrs
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was redissolved in 200 mL of CH2Cl2
  6. extractionThe reaction was extracted into CH2Cl2 and water
  7. concentrationThe organic phase was concentrated in vacuo
  8. custompurified via flash silica gel chromatography (EtOAc)

出典と根拠

ORDレコード
ord-74f3f754d7f94ff3805b15ea2e02c66c
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

関連ノート

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