Ethyl chloroformate → HCID 13520782, compound

HRID 847372Notes

Reaction equation

HRID 847372 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[O:11][C:12]1[CH:21]=[CH:20][C:15]([O:16][CH2:17][CH2:18][NH2:19])=[CH:14][CH:13]=1.C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[O:11][C:12]1[CH:21]=[CH:20][C:15]([O:16][CH2:17][CH2:18][NH:19][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 19881384HCID 19881384, compound

Product 1

HCID 13520782HCID 13520782, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

With stirring, a solution of 13 g of ethyl chloroformate in 20 ml of toluene is added dropwise to a solution of 24.8 g of 2-[4-(3-chlorophenoxy)phenoxy]ethylamine and 16.8 g ethyl diisopropylamine in 150 ml of toluene, and the mixture is thereafter stirred for 15 hours at this temperature. After cooling to room temperature, the reaction mixture is washed in succession with water, 1N hydrochloric acid and, finally, with a solution of sodium chloride and dried over sodium sulfate. The solvent is removed by vacuum distillation and the crude product is further purified by chromatography over silica gel with a 1:3 mixture of diethyl ether/hexane, affording the pure ethyl 2-[4-(3-chlorophenoxy)phenoxy]ethylcarbamate of m.p. 45°-46° C. The product so obtained is identical with that obtained in Example 1A.

Workup

  1. stirringthe mixture is thereafter stirred for 15 hours at this temperature
  2. washthe reaction mixture is washed in succession with water, 1N hydrochloric acid
  3. dry with materialfinally, with a solution of sodium chloride and dried over sodium sulfate
  4. customThe solvent is removed by vacuum distillation
  5. customthe crude product is further purified by chromatography over silica gel with a 1:3 mixture of diethyl ether/hexane

Sources & evidence

ORD record
ord-b1c4049a68b04818852eba44ed4bca24
Source dataset
uspto-grants-1992_08
Patent number
US05141956

Reaction notes

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