Toluene → benzyl N,N-bis(prop-2-yn-1-yl)carbamate

HRID 241820Notes

Reaction equation

HRID 241820 reaction equation
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].[CH2:7]([NH:10][CH2:11][C:12]#[CH:13])[C:8]#[CH:9].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:20]([O:4][C:1](=[O:2])[N:10]([CH2:11][C:12]#[CH:13])[CH2:7][C:8]#[CH:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 23350Dipropargylamine

Product 1

HCID 14358054benzyl N,N-bis(prop-2-yn-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.) solution of K2CO3 (4 Kg, 29.0 mol) in water (17.5 L) and toluene (12.5 L) was added dipropargylamine (2.50 Kg, 26.88 mol). Benzyloxychloroformate (4.8 Kg, 28.14 mol) was added at a rate such that T<10° C. The solution was stirred at 5° C. for 10 mins and then allowed to warm to RT. The aqueous phase was separated and the organic phase was washed with 0.2M HCl (12.5 L), sat NaHCO3 (13.5 L) and brine (17 L) and the resultant solution used in step 7 (assayed to contain 6.23 Kg, 102% based on an evaporated portion).

Workup

  1. temperatureto warm to RT
  2. customThe aqueous phase was separated
  3. washthe organic phase was washed with 0.2M HCl (12.5 L)

Sources & evidence

ORD record
ord-3daf4685ac914c6393d76c72494c70ed
Source dataset
uspto-grants-2014_02
Patent number
US08653084B2

Reaction notes

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