Hydrazine hydrate (1:1) → HCID 68615685, compound

HRID 971314Notes

Reaction equation

HRID 971314 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:23][C:24]([O:26]C)=O)[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.O.[NH2:29][NH2:30]>CO>[NH:29]([C:24](=[O:26])[CH2:23][N:15]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[NH2:30]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86591780HCID 86591780, compound

Product 1

HCID 68615685HCID 68615685, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude carboxylic acid methyl ester resulting from the precedent step, e.g. methyl ({[4-(2-methoxyethoxy)phenyl]sulfonyl}-4-methylanilino)acetate (1 mmol), was dissolved in MeOH (3.5 mL). Hydrazine hydrate was added (0.385 mL). The reaction mixture was stirred overnight at room temperature. Solvents were evaporated. The crude product was dissolved in ethyl acetate (4 mL) and was washed with water (4 mL). Aqueous phase was extracted with ethyl acetate (3×2 mL) and with methylene chloride (2×2 mL). Combined organic phases were dried over magnesium sulfate, filtrated and solvents were evaporated. The desired product, e.g. N-(2-hydrazino-2-oxoethyl)-4-(2-methoxyethoxy)-N-(4-methylphenyl)benzenesulfonamide was isolated as a light yellow oil, in 86% purity by HPLC (MaxPlot detection between 230 and 400 m). This intermediate was used in the next step without further purification.

Workup

  1. customSolvents were evaporated
  2. dissolutionThe crude product was dissolved in ethyl acetate (4 mL)
  3. washwas washed with water (4 mL)
  4. extractionAqueous phase was extracted with ethyl acetate (3×2 mL) and with methylene chloride (2×2 mL)
  5. dry with materialCombined organic phases were dried over magnesium sulfate
  6. filtrationfiltrated
  7. customsolvents were evaporated

Sources & evidence

ORD record
ord-357253763ecd412894e41066ff8cb57f
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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