Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 11362084, compound

HRID 602740Notes

Reaction equation

HRID 602740 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=O)[CH2:6]1.Cl.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[CH:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:5]1[CH2:10][CH2:9][C:8]2[C:28]3[C:27](=[CH:26][CH:25]=[C:24]([Cl:23])[CH:29]=3)[NH:30][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 11088194Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 11362084HCID 11362084, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To 5 g (0.016 mol) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester in glacial acetic acid (30 mL), 3.17 g (0.018 mol, 1.1 eq) of 4-chlorophenylhydrazine hydrochloride were added and the reaction mixture was stirred at 40° C. for 2 hours. An aqueous solution of NaHCO3 was added until pH=7 was reached, and the mixture was extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. A column chromatography on silica gel followed by a trituration from Et2O yielded 4.3 g (64%) of benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-acetic acid methyl ester as a racemic mixture of diastereomers, light brown crystals, MS: 418 (MH+).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4a43005e04494038aa93ad88ebcde0a1
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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