1,3-Dibromo-5,5-dimethylhydantoin → HCID 13911115, compound

HRID 651946Notes

Reaction equation

HRID 651946 reaction equation
[C:1]([O:9][C@@H:10]1[C@@:34]2([CH3:35])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13][C@@H:12]([O:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=O)C(C)(C)N(Br)C1=O>CCCCCC>[C:1]([O:9][C@@H:10]1[C@@:34]2([CH3:35])[C:14](=[CH:15][CH:16]=[C:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13][C@@H:12]([O:37][C:38](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 13911113HCID 13911113, compound

Product 1

HCID 13911115HCID 13911115, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of the dibenzoate described in (a) (0.58 gms) in hexane (10 ml) was treated with dibromodimethylhydantoin (0.15 gms) and heated under reflux for 25 mins. After cooling the mixture was filtered and the filtrate concentrated to a pale oil. The oil was dissolved in dry xylene (3 mls) and added dropwise to a refluxing solution of trimethylphosphite (0.4 ml) in xylene (5 ml.). Heating under reflux continued for 1.75 hrs. after which time the solvents were removed under reduced pressure and the residue crystallized from acetone/methanol to give the title compound. Recrystallized from ethanol/acetone the product had melting point 161°-162°⟦alpha⟧sub.D -8°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 25 mins
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate concentrated to a pale oil
  6. dissolutionThe oil was dissolved in dry xylene (3 mls)
  7. additionadded dropwise to a refluxing solution of trimethylphosphite (0.4 ml) in xylene (5 ml.)
  8. temperatureHeating
  9. temperatureunder reflux
  10. customafter which time the solvents were removed under reduced pressure
  11. customthe residue crystallized from acetone/methanol

Sources & evidence

ORD record
ord-195ecec97ba341639b1dd76fe3275b47
Source dataset
uspto-grants-1987_06
Patent number
US04670190

Reaction notes

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