Diethanolamine → HCID 23036187, compound

HRID 1709636Notes

Reaction equation

HRID 1709636 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH:27]([CH2:31][CH2:32][OH:33])[CH2:28][CH2:29][OH:30]>C1C=CC=CC=1>[OH:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][OH:33])[C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 728713-Benzoylpropionic acid

Product 1

HCID 23036187HCID 23036187, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension is prepared containing 17.8 grams (0.1 mole)-β-benzoyl-propionic acid in 500 ml of anhydrous benzene; then are added in this order and at room temperature 10.5 grams triethylamine, 15 grams ethyl chlorocarbonate and 21 grams (0.2 moles) diethanolamine. The suspension is stirred for over two hours, always at room temperature, and it is then filtered to remove the triethylamine hydrochloride. The liquid is concentrated, at reduced pressure, to about half of the initial volume and it is left to rest about 12 hours at 5°-10° C. temperature. The crystallized solid is filtered, vacuum dried at reduced pressure, about 40° C., and is recrystallized from ethanol. 17.5 grams of N,N-bis(2- hydroxy-ethyl)-β-benzoyl-propionamide with m.p. 98° C. are obtained.

Workup

  1. customA suspension is prepared
  2. filtrationit is then filtered
  3. customto remove the triethylamine hydrochloride
  4. concentrationThe liquid is concentrated, at reduced pressure, to about half of the initial volume and it
  5. waitis left
  6. waitto rest about 12 hours at 5°-10° C.
  7. filtrationThe crystallized solid is filtered
  8. customvacuum dried at reduced pressure, about 40° C.
  9. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-c92238b987464fb1bc7e3a0dda32b957
Source dataset
uspto-grants-1990_08
Patent number
US04950669

Reaction notes

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