Dimethylformamide → HCID 69955571, compound

HRID 650594Notes

Reaction equation

HRID 650594 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6](=[C:10]1[C:19]2[CH:18]=[C:17]([C:20]([NH2:22])=O)[S:16][C:15]=2[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7][CH2:8][CH3:9].CN(C)C=O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH:6](=[C:10]1[C:19]2[CH:18]=[C:17]([C:20]#[N:22])[S:16][C:15]=2[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 54472013HCID 54472013, compound

Product 1

HCID 69955571HCID 69955571, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (0.30 ml) was added to a mixture of 4-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamide (0.55 g) and dimethylformamide (DMF) (6 ml) with ice-water cooling under nitrogen atmosphere, and the mixture was stirred under the same condition for 1 hour. The reaction mixture was poured into an ice-cooled mixture of an aqueous solution of NaHCO3 and AcOEt to precipitate. The precipitate was collected by filtration, washed with water, and dried in vacuo to give 4-n-butylidene-5,6,7,8-tetrahydro-2-cyano-4H-cyclohepta[b]thiophene (0.42 g), which was immediately used in the next reaction.

Workup

  1. temperaturecooled
  2. customto precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2ce3a8b39bec4616bc7065132e298f15
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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