2-Methoxyethyl carbamate → HCID 14365707, compound

HRID 1649929Notes

Reaction equation

HRID 1649929 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:8])[NH2:7].[N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18])=[C:10]=[O:11]>[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:8])[NH:7][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:9]=[C:10]=[O:11]

Participants

4

Reactant 2

HCID 153752-Methoxyethyl carbamateHCID 637665HCID 637665, compound

Product 1

HCID 14365707HCID 14365707, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
60 °C

Procedure

6.65 g (0.05 mol) of carbamic acid-β-methoxyethyl ester and 0.15 g of zinc chloride were heated to 50° C. 8.8 g (0.05 mol) of 6-isocyanato-caproyl chloride were added dropwise to the resulting melt. Nitrogen was passed through the mixture while it was heated to 60° C. for 3 hours and then to 100° C. for 26 hours. The reaction was then terminated (IR control). The mixture was cooled, taken up in 100 ml of toluene and decanted to remove insoluble constituents; the toluene was removed under vacuum. 11 g of a colorless oil was obtained, which solidified to a waxy solid. Yield: 11 g=85%

Workup

  1. customThe reaction was then terminated (IR control)
  2. temperatureThe mixture was cooled
  3. customdecanted
  4. customto remove insoluble constituents
  5. customthe toluene was removed under vacuum

Sources & evidence

ORD record
ord-8798b11be9ff4f688d7e30d2244d7284
Source dataset
uspto-grants-1990_05
Patent number
US04921996

Reaction notes

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