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Phosgene → 2-(Chlorocarbonyl)-2-[2-(2-methylthioethoxy)-phenyl]-hydrazinecarboxylic acid methyl ester

HRID 4245
Notes
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Reaction equation

HRID 4245 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][O:6][C:7]([NH:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][CH2:19][S:20][CH3:21])=[O:8]>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]([NH:9][N:10]([C:1]([Cl:4])=[O:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][CH2:19][S:20][CH3:21])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 538333612-[2-(Methylthioethoxy)-phenyl]-hydrazinecarboxylic acid methyl ester

Product 1

HCID 541951662-(Chlorocarbonyl)-2-[2-(2-methylthioethoxy)-phenyl]-hydrazinecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

80 ml of a 20% solution of phosgene in toluene are added at 20° C. to 14.1 g of 2-[2-(2-methylthioethoxy)-phenyl]-hydrazinecarboxylic acid methyl ester in 130 ml of toluene. The reaction mixture is subsequently heated for 3 hours at 90° C., and the solvent is then removed. Recrystallisation of the residue in ethyl alcohol yields the compound No. 1.1 of the formula ##STR63## having a melting point of 55°-57° C.

Workup

  1. customthe solvent is then removed
  2. customRecrystallisation of the residue in ethyl alcohol
  3. customyields the compound No

Sources & evidence

ORD record
ord-f06ba04cb6474d75ba73dea89e898e68
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04725302

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes