Ethanol → Ethyl (ethoxycarbonyl)methanimidate

HRID 2058615Notes

Reaction equation

HRID 2058615 reaction equation
[CH:1]([O-:6])([O-])[O:2][CH2:3][CH3:4].[NH2:7][C:8]([O:10][CH2:11][CH3:12])=O.S(=O)(=O)(O)O.C(O)C>C1(C)C=CC=CC=1>[CH2:11]([O:10][CH:8]=[N:7][C:1]([O:2][CH2:3][CH3:4])=[O:6])[CH3:12]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5641Carbamic acid, ethyl esterHCID 53630039Ethylorthoformate

Product 1

HCID 53836390Ethyl (ethoxycarbonyl)methanimidateYield 38.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 40 ml toluene was dissolved 44.4 g (0.3 mol) of ethyl orthoformate, and while keeping the temperature at 110°-120° C., 18 g (0.2 ml) of urethane and 200 ml of a mixture of sulfuric acid with toluene were dropped thereto spending about 2 hours, during which produced ethanol was distilled out of the reaction vessel. After the dropping had been finished, toluene was removed by distillation. The intended product (9.5 g) was obtained by distillation of the residue; b.p. 72.4° C. (15 mmHg), yield 38.8%.

Workup

  1. customat 110°-120° C.
  2. distillationwas distilled out of the reaction vessel
  3. customtoluene was removed by distillation

Sources & evidence

ORD record
ord-ade2189a369d453b80f81b1e2c22fdff
Source dataset
uspto-grants-1982_03
Patent number
US04318731

Reaction notes

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