Acetone → HCID 23298004, compound

HRID 1953789Notes

Reaction equation

HRID 1953789 reaction equation
CC(C)=O.[CH3:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([N+:16]([O-])=O)[C:7]=1[NH:19][C:20](=[O:26])[C:21](OCC)=[O:22]>Cl.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[F:13][C:12]([F:15])([F:14])[C:10]1[CH:9]=[C:8]2[C:7]([NH:19][C:20](=[O:26])[C:21](=[O:22])[NH:16]2)=[C:6]([CH3:5])[CH:11]=1

Participants

6

Reactant 2

HCID 180Acetone2×HCID 23297991HCID 23297991, compound

Product 1

HCID 23298004HCID 23298004, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalyst2×HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

355 ml of a 15% titanium trichloride solution in aqueous hydrochloric acid are dissolved in 850 ml of water and 850 ml of acetone under a nitrogen atmosphere at 0° C. A solution of 35.5 g (110.8 mmol) of ethyl N-(2-methyl-6-nitro-4-trifluoromethylphenyl)oxamate in 1.7 1 of acetone is slowly added dropwise. The resulting violet solution is stirred at 0° C. for 16 hours. 15% titanium trichloride solution in aqueous hydrochloric acid is then added until, according to 1H-NMR analysis, starting material is no longer detectable. The reaction mixture is filtered off on a suction filter, the filtrate is concentrated and the deposited solid is filtered off again on a suction filter. The crude product is washed with dilute hydrochloric acid and water. The title compound is obtained as a white solid.

Workup

  1. customat 0° C
  2. filtrationThe reaction mixture is filtered off on a suction
  3. filtrationfilter
  4. concentrationthe filtrate is concentrated
  5. filtrationthe deposited solid is filtered off again on a suction
  6. filtrationfilter
  7. washThe crude product is washed with dilute hydrochloric acid and water

Sources & evidence

ORD record
ord-5bb191f965154a61b8ae24d3e2541611
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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