Ethylene Glycol → HCID 21224829, compound

HRID 1856850Notes

Reaction equation

HRID 1856850 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:19]=[O:20])[N:5]([CH2:8][C:9]2[C:17]([Cl:18])=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)[C:6]=1[Br:7].C1(C)C=CC=CC=1.[CH2:28](O)[CH2:29][OH:30]>C(OC(C)C)(C)C>[Br:1][C:2]1[N:3]=[C:4]([CH:19]2[O:30][CH2:29][CH2:28][O:20]2)[N:5]([CH2:8][C:9]2[C:17]([Cl:18])=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 22133001HCID 22133001, compound

Product 1

HCID 21224829HCID 21224829, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

The product obtained in Stage 2 above is introduced into 200 ml of toluene, 20 ml of ethylene glycol is added and the reaction medium is taken to reflux overnight then evaporated to dryness. 200 ml of a saturated solution of sodium hydrogen carbonate is added which is extracted 3 times with 200 ml of ethyl acetate. The organic phase is washed with saturated sodium chloride, then dried and evaporated to dryness. The residue obtained is impasted in isopropyl ether, filtered and dried. In this way 13.5 g of expected product (solid) is obtained. M.p.=188° C.

Workup

  1. additionis added
  2. temperatureto reflux overnight
  3. customthen evaporated to dryness
  4. addition200 ml of a saturated solution of sodium hydrogen carbonate is added which
  5. extractionis extracted 3 times with 200 ml of ethyl acetate
  6. washThe organic phase is washed with saturated sodium chloride
  7. customdried
  8. customevaporated to dryness
  9. customThe residue obtained
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-d82838c74a704301ab36dc66abf217a8
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

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