2,4,5-T-sodium → HCID 54304081, compound

HRID 372346Notes

Reaction equation

HRID 372346 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9](=[O:13])[NH:10][CH2:11]Cl.[Cl:14][C:15]1[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[CH:22][C:16]=1[O:17][CH2:18][C:19]([O-:21])=[O:20].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([NH:10][CH2:11][O:21][C:19](=[O:20])[CH2:18][O:17][C:16]1[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:15]=1[Cl:14])=[O:13]

Participants

4

Reactant 2

HCID 236757872,4,5-T-sodiumHCID 53741911HCID 53741911, compound

Product 1

HCID 54304081HCID 54304081, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 220 g (1 mole) of N-chloromethylcarbamic acid 2-chlorophenyl ester in 1 liter of anhydrous acetonitrile was added dropwise to a suspension of 277.5 g (1 mole) of sodium 2,4,5-trichlorophenoxyacetate in 2 liters of anhydrous acetonitrile. After the exothermic reaction had subsided, the mixture was stirred for a further 15 hours at room temperature. It was then filtered and the filtrate was concentrated in vacuo by distilling off the solvent. The residue was recrystallised from ether/benzine. 354 g (80.6% of theory) of 2-(2,4,5-trichlorophenoxy)-acetic acid 2-chlorophenoxycarbonylaminomethyl ester were obtained in the form of white crystals of melting point 119° C.

Workup

  1. customAfter the exothermic reaction
  2. filtrationIt was then filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. distillationby distilling off the solvent
  5. customThe residue was recrystallised from ether/benzine

Sources & evidence

ORD record
ord-a22e5c832c7f4a25b0d984312d95a6cc
Source dataset
uspto-grants-1978_05
Patent number
US04090862

Reaction notes

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