Hydrazine hydrate (1:1) → N-(5-aminoacetylamino-4-nitro-2-phenoxyphenyl)methanesulfonamide

HRID 441127Notes

Reaction equation

HRID 441127 reaction equation
[N+:1]([C:4]1[C:9]([NH:10][C:11](=[O:24])[CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][C:7]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:6]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:5]=1)([O-:3])=[O:2].O.NN>ClCCl.CO>[NH2:13][CH2:12][C:11]([NH:10][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:7]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:8]=1)=[O:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22406108N-(4-nitro-2-phenoxy-5-phthalimidoacetylaminophenyl)methanesulfonamide

Product 1

HCID 22406110N-(5-aminoacetylamino-4-nitro-2-phenoxyphenyl)methanesulfonamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To 350 ml of a dichloromethane-methanol (5:2) solution containing 9.5 g of N-(4-nitro-2-phenoxy-5-phthalimidoacetylaminophenyl)methanesulfonamide was added 0.64 ml of 99% hydrazine monohydrate at room temperature, followed by stirring for 19 hours. The precipitate was removed by filtration, followed by washing with hot acetonitrile. The filtrate was washed with water, and concentrated under reduced pressere. The resulting precipitate was washed with ethanol and dried to give 5.2 g of N-(5-aminoacetylamino-4-nitro-2 -phenoxyphenyl)methanesulfonamide as yellow crystals.

Workup

  1. customThe precipitate was removed by filtration
  2. washby washing with hot acetonitrile
  3. washThe filtrate was washed with water
  4. concentrationconcentrated under reduced pressere
  5. washThe resulting precipitate was washed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-a8948d2e22914161856ac9ca49e3a941
Source dataset
uspto-grants-1996_05
Patent number
US05521311

Reaction notes

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