Dimethylformamide → HCID 14836209, compound

HRID 1087754Notes

Reaction equation

HRID 1087754 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2]1.[O-:14][C:15]#[N:16].[K+].CN(C=O)C>[Br-].C([N+](CC)(CC)CC)C.O>[CH2:4]([CH:3]1[O:1][C:15](=[O:14])[NH:16][CH2:2]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 178581,2-EpoxydodecaneHCID 11378442Potassium cyanate

Product 1

HCID 14836209HCID 14836209, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

4.6 g of 1,2-epoxydodecane, 12.2 g of potassium cyanate, 25 ml of DMF, 0.2 g of tetraethylammonium bromide and 1.8 ml of water were stirred and heated at 120°-130° C. for 5 hours. The disappearance of the epoxide was followed by thin layer chromatography (tlc). The cooled reaction mixtre was poured into 200 ml of water and this was extracted with ethyl acetate. The combined organic extracts were washed with water, followed by brine, dried and concentrated to give a solid. Recrystallization from methylene chloride/hexane gave 3.7 g (65.2%) of product, m.p. 86°-87° C.

Workup

  1. temperatureheated at 120°-130° C. for 5 hours
  2. customThe cooled reaction mixtre
  3. extractionthis was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto give a solid
  8. customRecrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-85f25c6656d940ce8161f1deff058543
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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