Hydrochloric Acid → 5-phenyl-1H-thieno[3,2-c]pyrazole

HRID 2078717Notes

Reaction equation

[C:1]1([C:7]2[S:14][C:13]3[CH:12]=[N:11][N:10](C(=O)C)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([C:7]2[S:14][C:13]3[CH:12]=[N:11][NH:10][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 1-(5-phenyl-thieno[3,2-c]pyrazol-1-yl)-ethanone [3.82 g, 15.8 mmol, Intermediate (44)] and ethanol (50 mL) was added 6 N hydrochloric acid (50.0 mL, 300 mmol) in one portion and the resulting mixture heated at 70° C. After 18 hours, the reaction was cooled to ambient temperature and neutralized with 25% aqueous potassium carbonate. The mixture was diluted with water (200 mL) and aged at 0° C. for 1 hour. The resulting solid was collected, washed three times with water (50 mL), and then dried under vacuum to give 5-phenyl-1H-thieno[3,2-c]pyrazole [2.93 g, 92%, Intermediate (45)] as a beige powder. LC/MS: 201.0 (M+H), RT=3.15 minutes).

Workup

waitaged at 0° C. for 1 hour
customThe resulting solid was collected
washwashed three times with water (50 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-6b1eabc10bbc492da91a9561fe4e5315
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928231B2

Reaction notes

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