Hydrazine → 3-(Pyrrolidine-1-sulfonyl)benzohydrazide

HRID 877635Notes

Reaction equation

HRID 877635 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12](OC)=[O:13])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:19][NH2:20]>CO>[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:19][NH2:20])=[O:13])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 1216839HCID 1216839, compound

Product 1

HCID 23180693-(Pyrrolidine-1-sulfonyl)benzohydrazideYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-(pyrrolidin-1-ylsulfonyl)benzoate (150 mg, 0.557 mmol) was added to the hydrazine (35.7 mg, 1.114 mmol) in methanol and refluxed for 12 h at 65° C. Following cooling, reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography to yield 3-(pyrrolidin-1-ylsulfonyl)benzohydrazide (110 mg, 0.396 mmol, 71.1% yield). 1H NMR (CDCl3, 400 MHz): δ 8.18 (m, 1H), 8.03 (d, 1H, J=7.6 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.78 (bs, 1H), 7.63 (t, 1H, J=7.6 Hz), 4.17 (bs, 2H), 3.25 (m, 4H), 1.77 (m, 4H). Mass [M+H]+: 270.1

Workup

  1. temperatureFollowing cooling
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customcompound was purified by column chromatography

Sources & evidence

ORD record
ord-249d6a7c5b7a479f81e5c28176569d38
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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