Benzenesulfonyl hydrazide → HCID 86609401, compound

HRID 2215938Notes

Reaction equation

HRID 2215938 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=O)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[C:22]1([S:28]([NH:31][NH2:32])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.Cl>[C:22]1([S:28]([NH:31][N:32]=[C:12]2[CH2:11][CH2:10][C@H:9]3[C@@H:8]4[C@H:17]([CH2:16][CH2:15][C@:13]23[CH3:14])[C:18]2[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:6][CH2:7]4)(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 65723Benzenesulfonyl hydrazideHCID 70926342445-27-4

Product 1

HCID 86609401HCID 86609401, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 5.68 g (20 mmol) of 3-methoxy-8α-estra-1,3,5(10)-trien-17-one and 4.30 g (25 mmol) of benzenesulfonic acid hydrazide in 70 ml of ethanol is mixed with 3 drops of concentrated hydrochloric acid and then allowed to react at a bath temperature of 80–90° C. for three hours while being stirred vigorously. After the reaction solution is cooled, the precipitated product is suctioned off, rewashed with a little cold ethanol, and the hydrazone is dried in a vacuum. 8.10 g (92%) of product, which melts at 183–185° C., is obtained.

Workup

  1. customto react at a bath temperature of 80–90° C. for three hours
  2. temperatureAfter the reaction solution is cooled
  3. dry with materialthe hydrazone is dried in a vacuum

Sources & evidence

ORD record
ord-1500d474d48f4111bfe87706b5118721
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

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