Trichloromethanethiol → N-Trichloromethylthio-N-(2-Ethoxyethyl)Trichloroacetamidine

HRID 905358Notes

Reaction equation

HRID 905358 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])[CH3:2].C(N(CC)CC)C.[Cl:20][C:21]([SH:24])([Cl:23])[Cl:22]>CCOCC>[Cl:20][C:21]([Cl:23])([Cl:22])[S:24][N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:7](=[NH:12])[C:8]([Cl:9])([Cl:11])[Cl:10]

Participants

5

Reactant 3

HCID 6390TrichloromethanethiolHCID 8471TriethylamineHCID 178467948(1Z)-Trichloro-N'-(2-ethoxyethyl)ethanimidamide

Product 1

HCID 13298357N-Trichloromethylthio-N-(2-Ethoxyethyl)TrichloroacetamidineYield 83.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 4.7 g (0.02 mole) N-(2-ethoxyethyl)trichloroacetamidine, 2.1 g (0.02 mole) triethylamine, and 50 ml ether, cooled in an ice bath, was added 3.8 g (0.02 mole) perchloromethylmercaptan over 15 minutes. The temperature rose from 1.5° C. to 8.5° C. The solution was stirred 11/4 hours longer, filtered and rotary evaporated to give 6.4 g solid. Recrystallization from petroleum ether (cooling in dry ice) gave 4.0 g (54% yield; mp 65°-66° C.). The structure was confirmed via IR and elemental analysis.

Workup

  1. customrose from 1.5° C. to 8.5° C
  2. filtrationfiltered
  3. customrotary evaporated

Sources & evidence

ORD record
ord-553b77b7a41a4e2a80271ecb11cc8073
Source dataset
uspto-grants-1983_12
Patent number
US04423246

Reaction notes

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