Hydrochloric Acid → HCID 19820415, compound

HRID 1030468Notes

Reaction equation

HRID 1030468 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[Cl:7][C:8]1[CH:33]=[CH:32][C:11]2[O:12][C:13]3[CH:31]=[CH:30][CH:29]=[CH:28][C:14]=3[CH2:15][CH2:16][N:17](CC3C=CC=CC=3)[CH2:18][CH2:19][O:20][C:10]=2[CH:9]=1.Cl>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:33]=[CH:32][C:11]2[O:12][C:13]3[CH:31]=[CH:30][CH:29]=[CH:28][C:14]=3[CH2:15][CH2:16][N:17]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:18][CH2:19][O:20][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 19820422HCID 19820422, compound

Product 1

HCID 19820415HCID 19820415, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.47 ml of chloroformic acid ethyl ester were added at room temperature to a solution of 4.17 g of 3-chloro-7,8,9,10-tetrahydro-8-phenylmethyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine in 390 ml of toluene. The mixture was heated to reflux overnight, and after cooling shaken with excess of 1N hydrochloric acid. The toluene layer was separated and the acid aqueous layer extracted with diethyl ether. The combined organic extracts were shaken with 1N hydrochloric acid and water, after which the organic layer was concentrated in vacuo and dried azeotropically to yield 3.78 g (95%) of ethyl 3-chloro-7,8,9,10-tetrahydro-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine-8-carboxylate. Rf 0.6 (silica; hexane-acetone 8:2).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureafter cooling
  4. customThe toluene layer was separated
  5. extractionthe acid aqueous layer extracted with diethyl ether
  6. concentrationafter which the organic layer was concentrated in vacuo
  7. customdried azeotropically

Sources & evidence

ORD record
ord-32e44016f5ef4c48b540d5d32cbc510d
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

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