Ethyl chloroformate → HCID 19881385, compound

HRID 2058273Notes

Reaction equation

HRID 2058273 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[Cl:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][C:14]2[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20][NH2:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.[CH2:26]([O:28][C:29](Cl)=[O:30])[CH3:27]>CC(C)=O>[CH2:26]([O:28][C:29](=[O:30])[NH:21][CH2:20][CH2:19][O:18][C:17]1[CH:22]=[CH:23][C:14]([O:13][C:12]2[CH:24]=[CH:25][C:9]([Cl:8])=[CH:10][CH:11]=2)=[CH:15][CH:16]=1)[CH3:27]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 23350139HCID 23350139, compound

Product 1

HCID 19881385HCID 19881385, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

18.4 g of potassium carbonate, 8.0 g of 2-[p-(p-chlorophenoxy)phenoxy]ethylamine hydrochloride and 16.0 g of chloroformic acid ethyl ester in 210 ml of acetone are heated to reflux with stirring for 7 hours. Undissolved salt is vacuum filtered and washed well with acetone. The filtrate is evaporated in vacuo. The crystalline residue remaining is dissolved in ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is recrystallized from diisopropyl ether to yield 7.3 g (81.5%) of 2-[p-(p-chlorophenoxy)phenoxy]ethylcarbamic acid ethyl ester, m.p.--99°-100° C.

Workup

  1. temperatureto reflux
  2. filtrationfiltered
  3. washwashed well with acetone
  4. customThe filtrate is evaporated in vacuo
  5. dissolutionThe crystalline residue remaining is dissolved in ethyl acetate
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7044d48056e64ca4b6bc5b0bcfc32fcc
Source dataset
uspto-grants-1980_07
Patent number
US04215139

Reaction notes

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