Triethylamine → HCID 12748785, compound

HRID 2071242Notes

Reaction equation

HRID 2071242 reaction equation
[C:1]1([CH:7]2[CH:12]([C:13]([OH:15])=[O:14])[O:11][C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:33]([N:35]([CH2:38][CH2:39][O:40][CH:41](O)[CH3:42])[CH2:36][CH3:37])[CH3:34]>C(Cl)(Cl)Cl.O>[C:1]1([CH:7]2[CH:12]([C:13]([O:15][CH2:42][CH2:41][O:40][CH2:39][CH2:38][N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])=[O:14])[O:11][C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12748779HCID 12748779, compoundHCID 21624289HCID 21624289, compound

Product 1

HCID 12748785HCID 12748785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 12.8 g of (3-phenyl-1,4-benzodioxan-2-yl)-carboxylic acid in 100 cc of CHCl3, 5.1 g of triethylamine are added. The mixture is chilled and 5.4 g of ethyl chlorocarbonate are added dropwise. After stirring for 15 minutes, 8.8 g of N,N-diethylaminoethoxyethanol are added. After 2 hours the mixture is treated with water, the organic phase is separated and dried over Na2SO4. The solvent is removed under vacuum and the residue is transformed in the corresponding citrate (m.p. 73°-74°, from isopropanol).

Workup

  1. additionare added
  2. temperatureThe mixture is chilled
  3. customthe organic phase is separated
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-f601bc52422648a2aa43ecb7656da025
Source dataset
uspto-grants-1977_09
Patent number
US04046762

Reaction notes

Loading…