Acetic Acid → HCID 22096787, compound

HRID 1458683Notes

Reaction equation

HRID 1458683 reaction equation
[CH2:1]1[O:3][CH2:2]1.[NH2:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:16](O)(=[O:18])[CH3:17]>>[OH:18][CH2:16][CH2:17][N:4]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:1][OH:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 6877Ethyl 2-aminobenzoate

Product 1

HCID 22096787HCID 22096787, compoundYield 53%

Procedure

Ethylene oxide (12 ml; 242 mmol) was added dropwise under ice cooling to a solution of 4.1 g (25 mmol) of ethyl 2-aminobenzoate in 25 ml of a 30% suspension of acetic acid, followed by stirring for 1 hour. After the resultant mixture was stirred at room temperature for 2 nights, the mixture was stirred for 2 hours while bubbling nitrogen gas therethrough. Sodium hydrogencarbonate was added to the mixture to neutralized the same. Sodium chloride was then added until saturation, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and the solvent was distilled out under reduced pressure. The residue was purified by chromatography on a silica gel column (n-hexane/ethyl acetate=1:1→0:1), whereby 3.4 g of a pale yellow oil were obtained (yield: 53%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customwhile bubbling nitrogen gas
  3. additionSodium hydrogencarbonate was added to the mixture
  4. additionSodium chloride was then added until saturation
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column (n-hexane/ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-8363f42b01bf4e43a7ff90daf23028f9
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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