1,3-Dichloro-5,5-dimethylhydantoin → HCID 178481948, compound

HRID 1722464Notes

Reaction equation

HRID 1722464 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([OH:9])[CH:4]=1.[Cl:12]N1C(C)(C)C(=O)N(Cl)C1=O>CCOCC>[F:11][C:2]([F:1])([F:10])[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([OH:9])[C:4]=1[Cl:12]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 178481944HCID 178481944, compound

Product 1

HCID 178481948HCID 178481948, compoundYield 171.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

1907 g (11.48 mol) of 5-trifluoromethyl-3-hydroxy-1-methylpyrazole was stirred with 8 kg of ether and cooled to 0° C. 1222 g (6.2 mol) of 1,3-dichloro-5,5-dimethylhydantoin was added in three equal portions and the mixture was allowed to cool to 0° C. after each addition. The mixture was stirred for 4 hours, washed with water, brine and water. All washes were extracted with ether and the combined ether solutions were dried with MgSO4 filtered, evaporated on a rotary evaporator and recrystallized from methylcyclohexane to give 2131 g of a tan solid, m.p. 136°-140° C.

Workup

  1. temperatureto cool to 0° C.
  2. additionafter each addition
  3. washwashed with water, brine and water
  4. extractionAll washes were extracted with ether
  5. dry with materialthe combined ether solutions were dried with MgSO4
  6. filtrationfiltered
  7. customevaporated on a rotary evaporator
  8. customrecrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-1d3917f95d8948f9a080808d358463e2
Source dataset
uspto-grants-1989_08
Patent number
US04855442

Reaction notes

Loading…