Propargyl alcohol → Prop-2-yn-1-yl (2,2-dimethylpropyl)carbamate

HRID 2414047Notes

Reaction equation

HRID 2414047 reaction equation
[CH2:1]([N:6]=[C:7]=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:9]([OH:12])[C:10]#[CH:11]>N1(C2CCCCCCC2)CCCCCCN1>[CH2:1]([NH:6][C:7](=[O:8])[O:12][CH2:9][C:10]#[CH:11])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 850112,2-Dimethylpropyl isocyanate

Product 1

HCID 13292612Prop-2-yn-1-yl (2,2-dimethylpropyl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 66583054DiazabicyclooctaneCatalyst

Procedure

4520 g (40 moles) of neopentylisocyanate and 1 g of diazabicyclooctane (Dabco) are heated to 80° C. (10 l flask) and 2240 g (40 moles) of propargyl alcohol are then added in the course of 1.5 hours. When the addition of the alcohol has ended, IR spectra are used to monitor whether the reaction is complete. When the NCO band has disappeared, the mixture is distilled under a high vacuum. 6395 g (95% of theory) of 2-propinyl N-neopentylcarbamate of boiling point: 85° C./40 mbar are obtained.

Workup

  1. additionare then added in the course of 1.5 hours
  2. distillationthe mixture is distilled under a high vacuum

Sources & evidence

ORD record
ord-e5fd2b85f7fd4f55802f2b6ef4a4fcfe
Source dataset
uspto-grants-1988_01
Patent number
US04721523

Reaction notes

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