Diethyl Ether → HCID 178526936, compound

HRID 1633255Notes

Reaction equation

HRID 1633255 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[S:8][CH:9]=[C:10](C(OCC)=[O:12])[C:3]=12.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1.C[CH2:26][O:27]CC.[OH-].[Na+]>C(O)CCC.O>[OH2:12].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:26](=[O:27])[C:7]3[C:2]([C:3]4[CH:10]=[CH:9][S:8][C:4]=4[NH:5][CH:6]=3)=[N:24]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 70624(4-Chlorophenyl)hydrazineHCID 20253595HCID 20253595, compound

Product 1

HCID 178526936HCID 178526936, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.2 g of ethyl 4-chloro-thieno[2,3-b]pyridine-3-carboxylate (prepared according to J. Heterocyclic Chem., 1977, 14, 807) and 2.08 g of 4-chlorophenylhydrazine in 50 ml of n-butanol is refluxed for 48 hours. The reaction mixture is cooled in an ice bath and the resulting precipitate is collected, washed with a small amount of n-butanol to yield a solid. The solid is treated with ether and 1N sodium hydroxide (20 ml) and water (50 ml). The aqueous phase is washed with ether, then neutralized with ammonium chloride (2 g) to precipitate a yellow solid. The solid is collected, washed with water and dried to yield 2-(4-chlorophenyl)-thieno[2,3-b]pyrazolo[3,4-d]pyridin-3(5H)-one hydrate, m.p. 310°-313°.

Workup

  1. temperatureis refluxed for 48 hours
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. customthe resulting precipitate is collected
  4. washwashed with a small amount of n-butanol
  5. customto yield a solid
  6. washThe aqueous phase is washed with ether
  7. customto precipitate a yellow solid
  8. customThe solid is collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-427292a79da844b49d2db7b4191fb767
Source dataset
uspto-grants-1984_10
Patent number
US04479955

Reaction notes

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