Tetrahydrofuran → HCID 71084709, compound

HRID 1051266Notes

Reaction equation

HRID 1051266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].O1CCCC1.[CH3:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([CH3:20])=[C:22]([N+:28]([O-:30])=[O:29])[CH:23]=2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 83904-Methyl-3-nitroanilineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 71084709HCID 71084709, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Chloro-4-isocyanato-2-(trifluoromethyl)benzene (9.97 g, 45.0 mmol) was stirred in a solvent of tetrahydrofuran (100 mL). The reaction solution was added with 4-methyl-3-nitroaniline (6.52 g, 42.9 mmol), followed by stirring for about 6 hours at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated solid was added with a mixed solution of ethyl acetate/hexane (1/5), followed by stirring for 2 hours or more. The resulting solid was filtered under reduced pressure, and washed with diethyl ether. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (14 g, 87%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe concentrated solid was added with a mixed solution of ethyl acetate/hexane (1/5)
  6. stirringby stirring for 2 hours or more
  7. filtrationThe resulting solid was filtered under reduced pressure
  8. washwashed with diethyl ether
  9. customThe filtered solid was dried
  10. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Sources & evidence

ORD record
ord-27c71ec2fc4147ddadd65d00a142428f
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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