Triethylamine → Benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate

HRID 1373508Notes

Reaction equation

HRID 1373508 reaction equation
[CH3:1][C:2]([NH2:7])([CH3:6])[CH2:3][S:4][CH3:5].[C:8](Cl)([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(N(CC)CC)C>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]([NH:7][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:6])[CH2:3][S:4][CH3:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 120973802-Propanamine, 2-methyl-1-(methylthio)-

Product 1

HCID 60134425Benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamateYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (300 ml) was dissolved 23.86 g (200 mmol) of 1,1-dimethyl-2-(methylthio)ethylamine, and 103.4 g (200 mmol) of a 30% solution of carbobenzoxy chloride in toluene and then a solution of 24.29 g (240 mmol) of triethylamine in tetrahydrofuran were slowly dropped thereinto under ice-cooling. After the resulting mixture was stirred at room temperature for 3 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 36.35 g (yield 72%) of benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate.

Workup

  1. temperatureunder ice-cooling
  2. customthe triethylamine hydrochloride precipitated
  3. filtrationwas filtered under reduced pressure
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d9557dd2f7654d90b75d355436069660
Source dataset
uspto-grants-2007_01
Patent number
US07161032B2

Reaction notes

Loading…