Toluene → HCID 18928110, compound

HRID 1599410Notes

Reaction equation

HRID 1599410 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[C:17](=O)[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[N:9]2[C:23]=1[CH3:24])=[O:5])[CH3:2].C(Cl)([Cl:27])=O.C1(C)C=CC=CC=1>CN(C=O)C>[Cl:27][C:17]1[C:8]2[N:9]([C:23]([CH3:24])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 15224969HCID 15224969, compound

Product 1

HCID 18928110HCID 18928110, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 2-ethoxycarbonyl-1-methyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (Example 1) (88 g, 259 mmol) in DMF (1.5 l) was dropwise added a solution of 28% phosgene in toluene (0.5 l, 960 mmol). The mixture was stirred at 50° C. for 1 h and overnight at 25° C. followed by evaporation in vacuo. The residue was stirred with ice-cooled water. The solid was collected by filtration and washed with water to yield 83,4 g (95%) of 4-chloro-2-ethoxycarbonyl-1-methyl-7trifluoromethylimidazo[1,2-a]quinoxaline. M.p. 182°-183° C.

Workup

  1. customfollowed by evaporation in vacuo
  2. stirringThe residue was stirred with ice-
  3. temperaturecooled water
  4. filtrationThe solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-dd4b7f82a9cb4d5081b999641f108541
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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