Hydrazine → N-tert-Butyl-3-(hydrazonomethyl)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide

HRID 1843280Notes

Reaction equation

[NH2:1][NH2:2].[C:3]([NH:7][C:8]([C:10]1[S:14][C:13]2[CH2:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:12]=2[C:11]=1[CH:20]=O)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([NH:7][C:8]([C:10]1[S:14][C:13]2[CH2:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:12]=2[C:11]=1[CH:20]=[N:1][NH2:2])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 85% aqueous hydrazine (10 mL) in THF (180 mL) was added 131f (5.6 g, 20.0 mmol) in anhydrous THF (20 mL) over a period of 5 minutes. See FIG. 15. It was stirred at 20° C. for 3 h. The reaction mixture was concentrated under reduced pressure to afford 131g as a black solid (6.0 g, yield: 95%, purity: 95%). MS-ESI: [M+H]+ 294.0

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-e488ee010f3349979ab34bd0170f03fe
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946213B2

Reaction notes

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