Triethylamine → N-[2-[(4-Chlorophenyl)thio]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester

HRID 745167Notes

Reaction equation

HRID 745167 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH:11][CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl>[C:26]1([O:25][C:23](=[O:24])[N:11]([CH2:10][CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]([CH3:14])[CH3:13])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 13655026N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine

Product 1

HCID 13655162N-[2-[(4-Chlorophenyl)thio]ethyl]-N-(1-methylethyl)carbamic acid phenyl esterYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 22.8 g (0.1 mole) of N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine (oil in Preparation 1) and 10.1 g (0.1 mole) of triethylamine in 300 ml of methylene chloride was added dropwise with stirring a solution of 15.7 g (0.1 mole) phenyl chloroformate in 100 ml of methylene chloride. The resulting solution was stirred overnight at room temperature. The methylene chloride layer was extracted with 5% sodium hydroxide solution followed by 1N sulfuric acid. The methylene chloride layer was concentrated to give an oil which crystallized to a white solid. Recrystallization from isopropyl ether gave white crystalline product, m.p. 54°-56° C. in 79.6% yield.

Workup

  1. extractionThe methylene chloride layer was extracted with 5% sodium hydroxide solution
  2. concentrationThe methylene chloride layer was concentrated
  3. customto give an oil which
  4. customcrystallized to a white solid
  5. customRecrystallization from isopropyl ether
  6. customgave white crystalline product, m.p. 54°-56° C. in 79.6% yield

Sources & evidence

ORD record
ord-b41300c27db64d059a523b1d2298f2cd
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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