Ethanol → HCID 89260527, compound

HRID 1051267Notes

Reaction equation

HRID 1051267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].C(O)C.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[NH2:19][C:14]1[CH:13]=[C:12]([NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=2)=[O:10])[CH:17]=[CH:16][C:15]=1[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 24287Tin tetrachlorideHCID 71084709HCID 71084709, compound

Product 1

HCID 89260527HCID 89260527, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(4-methyl-3-nitrophenyl)urea (7 g, 18.7 mmol) obtained in Step (1) above was stirred in a solvent of ethanol (100 mL). The reaction solution was added with tin chloride (II) dihydrate (12.68 g, 56.2 mmol), followed by stirring for about 4 hours at 80° C. 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, filtered, and concentrated under reduced pressure. The concentrated solid was added with a mixed solution of ethyl acetate/hexane (1/1), and stirred for 2 hours or more. The resulting solid was filtered under reduced pressure, washed with diethyl ether, and the filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (3.9 g, 61%).

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. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated solid was added with a mixed solution of ethyl acetate/hexane (1/1)
  7. stirringstirred for 2 hours or more
  8. filtrationThe resulting solid was filtered under reduced pressure
  9. washwashed with diethyl ether
  10. customthe filtered solid was dried
  11. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Sources & evidence

ORD record
ord-f6c346b5bc3b47c4b48e3f2c31084e5c
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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