Triethylamine → HCID 67127121, compound

HRID 874601Notes

Reaction equation

HRID 874601 reaction equation
[S:1](Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([NH2:17])[C:9]([NH2:16])=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].C(N(CC)CC)C>ClCCl>[Br:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2=[N:16][S:1][N:17]=[C:8]2[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 105389214-Bromo-5-(trifluoromethyl)benzene-1,2-diamine

Product 1

HCID 67127121HCID 67127121, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (373 mg, 3.1 mmol) in dichloromethane (0.8 mL) was added dropwise to a refluxing solution of diamine 18 (500 mg, 2.0 mmol) and triethylamine (794 mg, 7.8 mmol) in dichloromethane (8.0 mL). The mixture was refluxed with stirring for 4 h. The mixture was then cooled to room temperature, quenched with water (20 mL), and extracted with dichloromethane (3×75 mL). The combined extracts were dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-25% ethyl acetate in hexane) provided 19 (377 mg, 68%) as a solid: LRESIMS m/z 294.1.

Workup

  1. temperatureThe mixture was refluxed
  2. customquenched with water (20 mL)
  3. extractionextracted with dichloromethane (3×75 mL)
  4. dry with materialThe combined extracts were dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-489712db3fa345329b45f09775782093
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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