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

HRID 74993Notes

Reaction equation

HRID 74993 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-41758b50d1254cfbbb295978ea9022a8
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…