Hydrazine → 4-(Morpholinosulfonyl)benzohydrazide

HRID 877647Notes

Reaction equation

HRID 877647 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[NH2:20][NH2:21]>CO>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([NH:20][NH2:21])=[O:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 809900Methyl 4-(morpholin-4-ylsulfonyl)benzoate

Product 1

HCID 8643394-(Morpholinosulfonyl)benzohydrazideYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 4-(morpholinosulfonyl)benzoate (135 mg, 0.473 mmol) was added to the hydrazine (30.3 mg, 0.946 mmol) in methanol and refluxed for 8 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 flash chromatography (3% methanol/DCM) to yield the 4-(morpholinosulfonyl)benzohydrazide (102 mg, 0.350 mmol, 74.0% yield) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.94 (m, 2H), 7.79 (m, 2H), 3.72 (m, 4H), 2.99 (m, 4H). Mass [M+H]+:286.0

Workup

  1. temperatureFollowing cooling
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customcompound was purified by flash chromatography (3% methanol/DCM)

Sources & evidence

ORD record
ord-a4b4645566c543628626bf034a071288
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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