Dimethylformamide → HCID 69955571, compound

HRID 2289431Notes

Reaction equation

HRID 2289431 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, compound

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-8ac8151bf893485ea4019ea2d8e1e45e
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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