3-Chlorobenzohydrazide → HCID 54047230, compound

HRID 1105580Notes

Reaction equation

HRID 1105580 reaction equation
[P:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([S:5][CH2:6][CH3:7])([O:3][CH3:4])=[O:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][NH2:24])=[O:22]>CO.C(Cl)Cl>[P:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[N:24][NH:23][C:21](=[O:22])[C:20]2[CH:25]=[CH:26][CH:27]=[C:18]([Cl:17])[CH:19]=2)=[CH:13][CH:14]=1)([S:5][CH2:6][CH3:7])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 742893-ChlorobenzohydrazideHCID 53847050HCID 53847050, compound

Product 1

HCID 54047230HCID 54047230, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of O-methyl S-ethyl O-(4-formylphenyl) thiophosphate (0.02 mole) in methanol (50 ml) and 3-chlorobenzoylhydrazine (0.02 mole) are charged into a glass reaction vessel and the mixture is stirred at room temperature for a period of about 12 hours. After this time the reaction mixture is stripped of methanol under vacuum and the residue is dissolved in methylene chloride (100 ml) and the resulting solution is washed with water (75 ml), with aqueous sodium hydroxide (75 ml; 0.1 N) and again with water (75 ml). The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent to yield the desired product O-methyl S-ethyl O-[4-(3-chlorobenzoylhydrazonomethyl)phenyl] thiophosphate.

Workup

  1. washthe resulting solution is washed with water (75 ml), with aqueous sodium hydroxide (75 ml; 0.1 N) and again with water (75 ml)
  2. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-279b6ad497064beeaf3a227dc7e917b7
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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