Hydrazine hydrate (1:1) → 4-ethoxy-N-(2-hydrazino-1-methyl-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide

HRID 971321Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH:21]([CH3:26])[C:22](OC)=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].O.[NH2:28][NH2:29]>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH:21]([CH3:26])[C:22]([NH:28][NH2:29])=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

The crude carboxylic acid methyl ester, e.g. methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate (264 mg, 0.70 mmol), was dissolved in MeOH (2 mL). Hydrazine hydrate was added (0.44 mL). The reaction mixture was stirred overnight at 60° C. Solvents were evaporated. The crude mass was redissolved in MeOH and solvents were evaporated again. This process was repeated three times. The desired product, e.g. 4-ethoxy-N-(2-hydrazino-1-methyl-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide (138.4 mg, 52%) was isolated as a colorless solid in 91.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

customSolvents were evaporated
dissolutionThe crude mass was redissolved in MeOH
customsolvents were evaporated again

Sources & evidence

ORD record: ord-4845284f08b34d229f50e2e30bb8350a
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312358B2

Reaction notes

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