Ethylformamide → 2-trifluoromethyl-7-(N-ethyl-N-formylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene

HRID 1089674Notes

Reaction equation

HRID 1089674 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8][C:7]=2[CH:14]=1.[CH2:17]([NH:19][CH:20]=[O:21])[CH3:18]>C(O)=O>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH:10]([N:19]([CH2:17][CH3:18])[CH:20]=[O:21])[CH2:9][CH2:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 12319EthylformamideHCID 113451992-trifluoromethyl-6,7,8,9-tetrahydro-[5H]-benzocyclohepten-7-one

Product 1

HCID 145020652-trifluoromethyl-7-(N-ethyl-N-formylamino)-6,7,8,9-tetrahydro-[5H]-benzocyclohepteneYield 99.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 228.2 g of 2-trifluoromethyl-6,7,8,9-tetrahydro-[5H]-benzocyclohepten-7-one, 219 g of N-ethylformamide and 151 g of formic acid is heated under reflux for 14 hours. After concentration in vacuo, while heating on a bain-marie, the residue is taken up in 2300 ml of methylene chloride. After washing twice with 800 ml of water each time, the organic layer is dried over magnesium sulphate and, after filtration, the solvent is removed in vacuo. 283 g of 2-trifluoromethyl-7-(N-ethyl-N-formylamino)-6,7,8,9-tetrahydro-[5H]-benzocycloheptene are obtained in the form of an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 14 hours
  3. concentrationAfter concentration in vacuo
  4. temperaturewhile heating on a bain-marie
  5. washAfter washing twice with 800 ml of water each time
  6. dry with materialthe organic layer is dried over magnesium sulphate
  7. filtrationafter filtration
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d6be2dfc797d4afb9d42f33063c4756f
Source dataset
uspto-grants-1992_01
Patent number
US05079245

Reaction notes

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