Pyridine → HCID 14365707, compound

HRID 1649930Notes

Reaction equation

HRID 1649930 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10])=[C:2]=[O:3].[CH3:12][O:13][CH2:14][CH2:15][O:16][C:17](=[O:19])[NH2:18].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:12][O:13][CH2:14][CH2:15][O:16][C:17](=[O:19])[NH:18][C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[C:2]=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 153752-Methoxyethyl carbamateHCID 637665HCID 637665, compound

Product 1

HCID 14365707HCID 14365707, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
25 °C

Procedure

8.8 g (50 mmol) of 6-isocyanato-caproyl chloride were introduced into 25 ml of toluene. A mixture of 5.95 g (50 mmol) of carbamic acid-β-methoxyethyl ester, 3.96 g (50 mmol) of pyridine and 15 ml of toluene was added dropwise at 0° C. The mixture was stirred for 6 hours at 25° C. and then heated to 60° C. for 10 hours. It was diluted with 100 ml of toluene and extracted once with 50 ml of 0.1N HCl. The organic phase (MgSO4) was dried and filtered and the solvent was evaporated off. 5.1 g of a product similar in its properties to the product from Example 2 were obtained. Yield: 5.1 g=40%.

Workup

  1. additionwas added dropwise at 0° C
  2. temperatureheated to 60° C. for 10 hours
  3. extractionextracted once with 50 ml of 0.1N HCl
  4. dry with materialThe organic phase (MgSO4) was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-b93f74ecff2b476ba8e94c5dbe298faf
Source dataset
uspto-grants-1990_05
Patent number
US04921996

Reaction notes

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