Diphenyl Ether → 4-Oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

HRID 1268839Notes

Reaction equation

HRID 1268839 reaction equation
C1([O:7][C:8]2C=CC=CC=2)C=CC=CC=1.C([N:18](CCCC)CCCC)CCC.[C:27]([C:29]([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)=[CH:30]C(N=[N+]=[N-])=O)#[N:28]>C(Cl)Cl>[O:7]=[C:8]1[C:40]2[CH:39]=[CH:38][S:37][C:36]=2[C:29]([C:27]#[N:28])=[CH:30][NH:18]1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 7622TributylamineHCID 73446014HCID 73446014, compound

Product 1

HCID 184465784-Oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of diphenyl ether (1.5 L) and trin-butylamine (0.3 L) heated to an equilibrated temperature of 215° C. was dropwise added a solution of 3-cyano-3-thiophen-2-yl-acryloyl azide 23 (85 g, 0.416 mol) in CH2Cl2 (340 mL). The temperature was maintained between 210–215° C. during this time. Following addition, the reaction was stirred a further 30 min, then allowed to cool to room temperature, during which the pure product precipitated from solution. The product was filtered and washed with copious hexane. Drying the precipitate under vacuum provided 58.4 g of 24. 1H NMR (400 MHz, d6-DMSO) δ 12.36 (s, 1H), 8.27 (s, 1H), 7.81 (d, J=5 Hz, 1H), 7.57 (d, J=5 Hz 1H).

Workup

  1. temperatureThe temperature was maintained between 210–215° C. during this time
  2. additionaddition
  3. customprecipitated from solution
  4. filtrationThe product was filtered
  5. washwashed with copious hexane
  6. customDrying the precipitate under vacuum

Sources & evidence

ORD record
ord-2c1ece2332534e05844f1231f10f076f
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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