Hydrochloric Acid → 3-Allyl-5-benzyl-2-thiohydantoin

HRID 2075295Notes

Reaction equation

HRID 2075295 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH2:20]([N:23]=[C:24]=[S:25])[CH:21]=[CH2:22].Cl>O>[CH2:20]([N:23]1[C:10](=[O:12])[CH:2]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:1][C:24]1=[S:25])[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5971Allyl IsothiocyanateHCID 6140L-PhenylalanineHCID 8471Triethylamine

Product 1

HCID 31441923-Allyl-5-benzyl-2-thiohydantoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask equipped with a magnetic stirrer was charged with phenylalanine (15.8 g, 0.100 mol), triethylamine (11.1 g, 0.11 mol) pyridine (100 mL), and water (50 mL). Allyl isothiocyanate (10.4 g, 0.11 mol) was added to the flask, and the mixture was kept at 40-450 for 4 hr. the mixture was cooled to room temperature and was then extracted with 3×200 mL of toluene. The aqueous phase was mixed with concentrated hydrochloric acid (16 mL, 0.19 mol) and boiled gently for 45 min. The reaction mixture was stirred rapidly as it cooled to room temperature. It was further cooled in an ice-water bath for 20 min, and the solid that had formed was collected and washed with water.

Workup

  1. customA flask equipped with a magnetic stirrer
  2. extractionwas then extracted with 3×200 mL of toluene
  3. waitboiled gently for 45 min
  4. temperaturecooled to room temperature
  5. temperatureIt was further cooled in an ice-water bath for 20 min
  6. customthe solid that had formed
  7. customwas collected
  8. washwashed with water

Sources & evidence

ORD record
ord-a64712f2898d4161a5090360c1ddfb58
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

Loading…