Hydrazine → HCID 16412815, compound

HRID 877641Notes

Reaction equation

HRID 877641 reaction equation
[O:1]=[S:2]1(=[O:18])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11](OC)=[O:12])[CH2:4][CH2:3]1.[NH2:19][NH2:20]>CO>[O:1]=[S:2]1(=[O:18])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([NH:19][NH2:20])=[O:12])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 16413657HCID 16413657, compound

Product 1

HCID 16412815HCID 16412815, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-(1,1-dioxidothiomorpholino)benzoate (95 mg, 0.353 mmol) was added to the hydrazine (22.61 mg, 0.705 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 (2% CH3OH/CH2Cl2) afforded the title compound 3-(1,1-dioxidothiomorpholino)benzohydrazide (32 mg, 0.109 mmol, 31.0% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 7.34 (m, 1H), 7.29 (t, 1H, J=8.4 Hz), 7.18 (d, 1H, J=7.6 Hz), 6.70 (dd, 1H, J=4.8 & 8.0 Hz), 3.85 (m, 4H), 3.05 (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 (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-74d56d66a722452b9d0abd6a7fa89e16
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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