Hydrazine hydrate (1:1) → HCID 178466868, compound

HRID 1957949Notes

Reaction equation

HRID 1957949 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([NH2:9])=[NH:8])[CH3:3].O.[NH2:26]N>C(O)C>[CH2:2]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH2:22]2)(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([NH:9][NH2:26])=[NH:8])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 673509562-Ethoxy-5-(4-ethylpiperazin-1-yl-sulfonyl)benzamidine hydrochloride

Product 1

HCID 178466868HCID 178466868, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-ethoxy-5-(4-ethylpiperazin-1-yl-sulfonyl)benzamidine hydrochloride prepared in the above preparation example 1 was dissolved into ethanol (200 ml), and 85% hydrazine hydrate (5.9 g, 0.1 mol) was slowly dropped into the solution under ice bath. The mixture was stirred for 30 minutes and then at room temperature for 1 hour. Then, the solution was concentrated to dryness, and added with ethyl acetate to perform a recrystallization. The separated crystal was dried under vacuum to obtain 28 g of product with a yield of 74%. 1H NMR (CDCl3, 300 MHz) δ: 1.02 (3H, t), 1.49 (3H, t), 2.39 (2H, q), 2.51 (4H, t), 3.05 (4H, t), 4.18 (2H, q), 7.00 (1H, d), 7.69 (1H, dd), 8.13 (1H, d). ESI-MS m/z 356.3 (M++1, 100).

Workup

  1. additionwas slowly dropped into the solution under ice bath
  2. waitat room temperature for 1 hour
  3. concentrationThen, the solution was concentrated to dryness
  4. additionadded with ethyl acetate
  5. customa recrystallization
  6. customThe separated crystal was dried under vacuum

Sources & evidence

ORD record
ord-4e13d4efa975423b8ee9d26d921f38f0
Source dataset
uspto-grants-2013_04
Patent number
US08410098B2

Reaction notes

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