Acetic Acid → HCID 21433961, compound

HRID 2398744Notes

Reaction equation

HRID 2398744 reaction equation
[Na].Br[CH:3]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH:24]=1)[C:4]([O:6][CH2:7]C)=[O:5].[C:25](O)(=[O:27])C>CO.O>[CH3:25][O:27][CH:3]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH:24]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 21433970HCID 21433970, compound

Product 1

HCID 21433961HCID 21433961, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium (0.23 g.) was dissolved in dry methanol (60 ml.) and this solution added to ethyl 2-bromo-2-(p-chlorophenyl-5-benzoxazolyl)acetate (2.8 g.). The resulting solution was stirred for 68 hours at room temperature and then evaporated at 20° C. in vacuo to leave a residual oil. The oil was stirred in water (50 ml.) and the pH adjusted to 4 by the addition of glacial acetic acid. The resulting suspension was extracted with ether (3 × 75 ml.). The extracts were combined and washed with saturated sodium bisulphite solution (3 × 25 ml.). After drying (Na2SO4), the ether solution was evaporated to leave a gummy solid (2.15 g.). 1 Gram was purified by chromatography to yield a waxy solid (0.4 g.), which was subsequently recrystallised from carbon tetrachloride and 40°-60° petroleum ether. The resulting solid was the required product, m.p. 100°-105° C.

Workup

  1. customevaporated at 20° C. in vacuo
  2. customto leave a residual oil
  3. extractionThe resulting suspension was extracted with ether (3 × 75 ml.)
  4. washwashed with saturated sodium bisulphite solution (3 × 25 ml.)
  5. dry with materialAfter drying (Na2SO4)
  6. customthe ether solution was evaporated
  7. customto leave a gummy solid (2.15 g.)
  8. custom1 Gram was purified by chromatography
  9. customto yield a waxy solid (0.4 g.), which
  10. customwas subsequently recrystallised from carbon tetrachloride and 40°-60° petroleum ether

Sources & evidence

ORD record
ord-b4539d30a8f146a1b63afd9189468888
Source dataset
uspto-grants-1977_05
Patent number
US04025636

Reaction notes

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