Triethylamine → Phthalide

HRID 1658191Notes

Reaction equation

HRID 1658191 reaction equation
C(N(CC)CC)C.Br[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[O:12])[O:10]1>CC(C)=O>[C:11]1([C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][O:10]1)=[O:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 6885Phthalide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 6-tritylaminopenicillanic acid (9.8 g; 0.02M) in dry acetone (100 ml.) was cooled to 0°C, triethylamine (2.9 mg. 0.02 M) was added, followed by 3-bromophthalide (4.1 g; 0.02M) in dry acetone (20 ml.), and the reaction mixture kept at 0°C with stirring for 2 hours and finally at ambient temperatures for 1 hour. The triethylammonium bromide which precipitated was removed by filtration, the evaporated filtrate was dissolved in ethyl acetate (150 ml.) and after two washings with cold 2% aqueous sodium bicarbonate (2 × 150 ml.) and with ice-water (2 × 100 ml.) the ethyl acetate layer was dried over anhydrous magnesium sulphate to yield, on removal of solvent in vacuo, phthalide 6-tritylaminopenicillanate as a white amorphous solid.

Workup

  1. customkept at 0°C
  2. customThe triethylammonium bromide which precipitated
  3. customwas removed by filtration
  4. dissolutionthe evaporated filtrate was dissolved in ethyl acetate (150 ml.)
  5. washafter two washings with cold 2% aqueous sodium bicarbonate (2 × 150 ml.)
  6. dry with materialwith ice-water (2 × 100 ml.) the ethyl acetate layer was dried over anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-663d086fb34142a685f21f733463b869
Source dataset
uspto-grants-1976_06
Patent number
US03963702

Reaction notes

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