Diethyl Ether → HCID 14675603, compound

HRID 2352344Notes

Reaction equation

HRID 2352344 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[CH2:13]([N:15]=C=O)[CH3:14].C([O:20]CC)C>C(N(CC)CC)C>[OH:11][C:7]1[CH:6]=[C:5]([C@@H:4]([OH:12])[CH2:3][NH:2][C:1](=[O:20])[NH:15][CH2:13][CH3:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 6041PhenylephrineHCID 8022Ethyl isocyanate

Product 1

HCID 14675603HCID 14675603, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

To a suspension of R-phenylephrine (10.0 g, 59.8 mmol) in diethyl ether (200 ml) with triethylamine (4 drops) is added ethyl isocyanate (4.25 g, 59.8 mmol) in diethyl ether (50 ml). The reaction is allowed to stir overnight at room temperature. A white suspension forms which is decanted from the precipitated gum, filtered and dried giving 3.0 g (21% yield) of product, m.p. 102°-105° C.

Workup

  1. customA white suspension forms which is decanted from the precipitated gum
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-749cea4938c04b2b81bcffaaf00060dd
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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