2,4-Dichlorophenol → HCID 23465043, compound

HRID 838818Notes

Reaction equation

HRID 838818 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[CH3:17][O:18][C:19](=[O:30])[N:20]([CH2:28]Cl)[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1>C1C=CC=CC=1>[CH3:17][O:18][C:19](=[O:30])[N:20]([CH2:28][O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 8471TriethylamineHCID 23465032HCID 23465032, compound

Product 1

HCID 23465043HCID 23465043, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 16.3 g (0.1 mole) of 2,4-dichlorophenol and 14 ml (0.1 mole) of triethylamine in 100 ml of benzene was added dropwise, over the course of 15 minutes, to a solution of 23.4 g (0.1 mole) of Methyl-N-chloromethyl-N-(4-chlorophenyl)-carbamate in 200 ml of dry benzene. Thereafter the triethylamine hydrochloride was filtered off, the filtrate was washed with 5% strength sodium hydroxide solution and water, and after drying over calcined sodium sulphate the benzene was distilled off under reduced pressure. 52.4 g (92% of theory) of Methyl-N-(2,4-dichlorophenoxymethyl)-N-(4-chlorophenyl)-carbamate, melting at 70° - 80° C after recrystallization from ethanol, were obtained.

Workup

  1. filtrationThereafter the triethylamine hydrochloride was filtered off
  2. washthe filtrate was washed with 5% strength sodium hydroxide solution and water
  3. customafter drying
  4. distillationwas distilled off under reduced pressure
  5. custom52.4 g (92% of theory) of Methyl-N-(2,4-dichlorophenoxymethyl)-N-(4-chlorophenyl)-carbamate, melting at 70° - 80° C after recrystallization from ethanol
  6. customwere obtained

Sources & evidence

ORD record
ord-5b348a739b014a57bf006804ac3236e6
Source dataset
uspto-grants-1978_06
Patent number
US04093447

Reaction notes

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