Benzyl Chloride → HCID 58957437, compound

HRID 2075303Notes

Reaction equation

HRID 2075303 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[CH:7]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:6][C:5]1=[S:18])[CH:2]=[CH2:3].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[C:11]1([C:10]([O:17][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:7]2[NH:6][C:5](=[S:18])[N:4]([CH2:1][CH:2]=[CH2:3])[C:8]2=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 23665647Potassium tert-butoxideHCID 58957413HCID 58957413, compound

Product 1

HCID 58957437HCID 58957437, compoundYield 123.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-allyl-5-benzoyl-2-thiohydantoin (0.098 g, 0.0003 mol) and benzyl chloride (0.042 g, 0.00033 mol) in tetrahydrofuran (2 mL) was added a solution of 1M potassium tert-butoxide in tetrahydrofuran (0.33 mL, 0.00033 mol) under argon. A cherry solid was formed in the reaction mixture. The resulting mixture was heated at reflux for 1 hr and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (40 mL), washed with 3M HCl (2×20 mL) and brine (1×20 mL), filtered through 1 PS filter paper and concentrated under reduced pressure to give 0.13 g of a brown oil which solidified on standing. This solid was triturated with hexane (5 mL) once and then was dried under high vacuum. NMR (CDCl3) δ (10.9 s br, 1H), 8.6-8.9 (m, 2H), 7.3-7.9 (m, 8H), 4.7 (S, 2H), 4.4 (d, 2H).

Workup

  1. customA cherry solid was formed in the reaction mixture
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 1 hr
  4. washwashed with 3M HCl (2×20 mL) and brine (1×20 mL)
  5. filtrationfiltered through 1 PS
  6. filtrationfilter paper
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd6dd51637224b9baf020fbb240a88d6
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

Loading…