Benzoyl chloride → Benzoic acid 2-thioxo-oxazolidin-4-ylmethyl ester

HRID 1242273Notes

Reaction equation

HRID 1242273 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][CH:12]1[CH2:16][O:15][C:14](=[S:17])[NH:13]1.C(N(CC)CC)C>C1COCC1>[S:17]=[C:14]1[NH:13][CH:12]([CH2:11][O:10][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][O:15]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 219390744-Hydroxymethyl-1,3-oxazolidine-2-thione

Product 1

HCID 86601550Benzoic acid 2-thioxo-oxazolidin-4-ylmethyl esterYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzoyl chloride (14.6 mL, 126.1 mmol) in dry THF (50 mL) was added to a solution of 4-hydroxymethyl-1,3-oxazolidine-2-thione (14.0 g, 105.1 mmol) in dry THF (250 mL) and triethylamine (17.5 mL, 126.1 mmol) at 0° C. After 12 hours of stirring at room temperature, triethylamine hydrochloride was filtered off, and the solvent was distilled out in vacuo. The residue was purified by silica gel column chromatography eluted with ethyl acetate/acetone (1/1=v/v), followed by recrystallization from a mixed solvent [n-hexane/ethyl acetate (3/1=v/v)] to afford benzoic acid 2-thioxo-oxazolidin-4-ylmethyl ester as a colorless solid (20.5 g, 82%).

Workup

  1. filtrationtriethylamine hydrochloride was filtered off
  2. distillationthe solvent was distilled out in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluted with ethyl acetate/acetone (1/1=v/v)
  5. customfollowed by recrystallization from a mixed solvent [n-hexane/ethyl acetate (3/1=v/v)]

Sources & evidence

ORD record
ord-fe5da5bb56704f7bba37aa2011e3b673
Source dataset
uspto-grants-2006_10
Patent number
US07115705B2

Reaction notes

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