Benzaldehyde → HCID 6712635, compound

HRID 2075299Notes

Reaction equation

HRID 2075299 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[CH2:7][NH:6][C:5]1=[S:10])[CH:2]=[CH2:3].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.Cl>O>[CH2:1]([N:4]1[C:8](=[O:9])[C:7](=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:6][C:5]1=[S:10])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3032418Hydantoin, 3-allyl-2-thioxo-

Product 1

HCID 6712635HCID 6712635, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask equipped with a magnetic stirrer, condenser, and nitrogen pressure was charged with 3-allylthiohydantoin (15 g, 0.096 mol), water (90 mL), and benzaldehyde (10.2 g, 0.096 mol). As the mixture was stirred, triethylamine (19.4 g, 0.192 mol) was added slowly. After 18 hr, HPLC analysis indicated the absence of starting material, and the mixture was transferred to an Erlenmeyer flask. The mixture was stirred vigorously as 3 M hydrochloric acid was added dropwise until the pH reached 3 (65 mL). The mixture was stirred for an additional 90 min, and then the solid that had formed was collected by filtration. The still wet solid was resuspended in 100 mL of water, stirred for 30 min, and collected. After air drying, the orange solid weighed 18.4 g (79%). HPLC analysis indicated a purity of 95% at 215 nm. NMR (CDCl3) δ 9.3 (bs, 1H), 7.4 (s, 5H), 6.8 (s, 1H), 5.1-6.3 (m, 3H), 4.6 (d, 2H).

Workup

  1. customA flask equipped with a magnetic stirrer, condenser
  2. additionwas added dropwise until the pH
  3. stirringThe mixture was stirred for an additional 90 min
  4. customthe solid that had formed
  5. filtrationwas collected by filtration
  6. stirringstirred for 30 min
  7. customcollected
  8. customAfter air drying

Sources & evidence

ORD record
ord-31f81349e4524066a3f268c75c8c8479
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

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