Methylhydrazine → HCID 19917863, compound

HRID 1755895Notes

Reaction equation

HRID 1755895 reaction equation
[Br:1][C:2]1[C:7]2[O:8][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:6]=2[C:5]([Cl:23])=[C:4]([C:24]([NH:26][NH:27][C:28](=[O:44])[C:29]([CH3:43])([O:31][N:32]2C(=O)C3=CC=CC=C3C2=O)[CH3:30])=[O:25])[CH:3]=1.CNN>O1CCCC1>[ClH:23].[NH2:32][O:31][C:29]([CH3:43])([CH3:30])[C:28]([NH:27][NH:26][C:24]([C:4]1[CH:3]=[C:2]([Br:1])[C:7]2[O:8][C:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:10][C:6]=2[C:5]=1[Cl:23])=[O:25])=[O:44]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 19917874HCID 19917874, compound

Product 1

HCID 19917863HCID 19917863, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-[(7-Bromo-4-chloro-2,2-diphenyl-1,3-benzodioxol-5-yl)carbonyl]-2-[2-methyl-2-(phthalimidooxy)propionyl]hydrazine 500 mg (0.77 mmol) are dissolved in 10 ml of tetrahydrofuran and treated at 0° C. with 35 mg (0.77 mmol) of methylhydrazine. After stirring at 0° C. for 2 hours and stirring at room temperature for 3 hours the mixture is concentrated in a vacuum. The residue is chromatographed on 20 g of silica gel (0.06-02 mm). The product is eluted with dichloromethane/ethanol (95:5 v/v). The eluate is concentrated and the residue is treated with ethanolic hydrochloric acid. After crystallization from ethanol/diethyl ether there are obtained 220 mg of 1-[2-(aminooxy)-2-methylpropionyl]-2-[(7-bromo-4-chloro-2,2-diphenyl-1,3-benzodioxol-5-yl)carbonyl]hydrazine hydrochloride (1:1) as white crystals of melting point 216°-218° C.

Workup

  1. stirringstirring at room temperature for 3 hours the mixture
  2. concentrationis concentrated in a vacuum
  3. customThe residue is chromatographed on 20 g of silica gel (0.06-02 mm)
  4. washThe product is eluted with dichloromethane/ethanol (95:5 v/v)
  5. concentrationThe eluate is concentrated
  6. additionthe residue is treated with ethanolic hydrochloric acid
  7. customAfter crystallization from ethanol/diethyl ether there

Sources & evidence

ORD record
ord-bcbb8355103444f7af793fff6e6aca16
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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