反应详情

温度

5 °C

In advance, succinimidyl-S-benzoylmercaptoacetic acid (BMS) was synthesized as follows. Two-layer system of toluene (75 mL) and water (75 mL) was cooled in an ice-water bath, sodium hydroxide (8.86 g, 221.5 mmol) was added thereto. Next, mercaptoacetic acid (9.22 g, 100 mmol) was added dropwise and washed with 5 mL of water. Further, benzoyl chloride (14.61 g, 100.3 mmol) was added dropwise, and washed with 5 mL of toluene. The reaction was conducted with stirring at about 5° C. for 30 minutes, then at room temperature for 3.5 hours. The reaction mixture was subjected to separation, the organic layer was extracted in 3 times with 10 mL of water, and the aqueous layers were combined together. Under stirring, 12 mL of concentrated hydrochloric acid was added dropwise to the aqueous layer to adjust pH 1-2, and the crystals formed were collected by filtration. The crystals were dried in a desiccator, then washed with hexane, and dissolved in ethyl acetate. The solvent was distilled away to give S-benzoylmercaptoacetic acid (19.19 g, 97.8 mmol, 98% yield) as colorless needle-like crystals.

1. washwashed with 5 mL of water
2. washwashed with 5 mL of toluene
3. waitat room temperature for 3.5 hours
4. customThe reaction mixture was subjected to separation
5. extractionthe organic layer was extracted in 3 times with 10 mL of water
6. stirringUnder stirring
7. addition12 mL of concentrated hydrochloric acid was added dropwise to the aqueous layer
8. customthe crystals formed
9. filtrationwere collected by filtration
10. customThe crystals were dried in a desiccator
11. washwashed with hexane
12. dissolutiondissolved in ethyl acetate
13. distillationThe solvent was distilled away