Water → HCID 90020659, compound

HRID 2200177Notes

Reaction equation

HRID 2200177 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24].O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:22](=[O:25])[CH:23]=[CH2:24])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 27757093-Nitro-5-(trifluoromethyl)aniline

Product 1

HCID 90020659HCID 90020659, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-nitro-5-(trifluoromethyl)aniline (150 mg, 0.73 mmol), triethylamine (220 mg, 2.18 mmol) in DCM (8 mL), cool to 0° C. at ice bath, add slowly acryloyl chloride (198 mg, 2.18 mmol). After addition, stir the reaction at room temperature for 2 hrs. Pour the mixture into water (30 mL), extract with EtOAc (10 mL×3), combine the organic layers; wash with brine (50 mL), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product (190 mg) which is used without further purification.

Workup

  1. additionAfter addition
  2. customthe reaction at room temperature for 2 hrs
  3. extractionextract with EtOAc (10 mL×3)
  4. washwash with brine (50 mL)
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-e79d03ac3dad4424a1a3eb04c0e69932
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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