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

HRID 527021

반응식

HRID 527021 반응식
[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

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 860461-Methylcyclohex-3-ene-1-carboxylic acid2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-74f3f754d7f94ff3805b15ea2e02c66c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

연결된 노트

불러오는 중…