Ethyl chloroformate → HCID 86734757, compound

HRID 371725Notes

Reaction equation

HRID 371725 reaction equation
[C:1]1([CH2:13][C:14]([O-:16])=[O:15])([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(OCC)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>O.CC(C)=O.C(N(CC)CC)C>[N-:23]=[N+:24]=[N-:25].[C:1]1([CH2:13][C:14]([O-:16])=[O:15])([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 71401111[1-(2-Methoxy-2-oxoethyl)cycloheptyl]acetate

Product 1

HCID 86734757HCID 86734757, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent3×HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

15.9 g. monomethyl 1,1-cycloheptane-diacetate are dissolved in 100 ml. anhydrous acetone and, in a manner analogous to that described in Example 1, first mixed with 8.1 g. triethylamine in 30 ml. acetone, thereafter with 9.8 g. ethyl chloroformate in 30 ml. anhydrous acetone and finally with 6.5 g. sodium azide in 20 ml. water. After the reaction has taken place, the reaction mixture is extracted as in Example 1 and the solution obtained of monomethyl 1,1-cycloheptane-diacetate azide is rearranged in toluene to the isocyanate. The methyl 1-isocyanatomethyl-1-cycloheptane-acetate obtained is boiled for 3 hours under reflux in 20% hydrochloric acid. Upon evaporation in a vacuum, 1-aminomethyl-1-cycloheptane-acetic acid separates out in the form of its hydrochloride, which is recrystallised from methanol/acetone/ethyl acetate; m.p. 69° - 72° C.

Workup

  1. additionfirst mixed with 8.1 g
  2. extractionthe reaction mixture is extracted as in Example 1

Sources & evidence

ORD record
ord-8245d8f3c32e49b98d4d57015b1bfce1
Source dataset
uspto-grants-1978_05
Patent number
US04087544

Reaction notes

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