Triethylamine → HCID 57555385, compound

HRID 220978Notes

Reaction equation

HRID 220978 reaction equation
CC1[O:11][C:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3NCCC=2N=1.S(Cl)(Cl)=O.Cl.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C([N:34]([CH2:37][CH3:38])CC)C>C1(C)C=CC=CC=1.ClCCl>[C:37]([C:38]1[CH:13]=[CH:12][C:9]([C:10]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([C:22]([F:30])([F:31])[F:21])=[CH:24][CH:25]=2)=[O:11])=[CH:8][C:15]=1[CH3:14])#[N:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27239614-(Trifluoromethyl)anilinium chlorideHCID 231123652-methyl-5,6-dihydro-4H-benzo[b]oxazolo[5,4-d]azepine

Product 1

HCID 57555385HCID 57555385, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-cyano-3-methyl-benzoic acid from Example E6 (750 mg, 4.6 mmol) and thionyl chloride (1.02 ml, 14.0 mmol) in toluene (40 ml) was heated at reflux for 2 h. After cooling at room temperature, solvents were re-moved in vacuo and azeotroped with toluene. The residue was redissolved in dichloromethane (25 ml) then 4-trifluoromethylaniline hydrochloride (1.11 g, 5.6 mmol) in dichloromethane (5 ml) and triethylamine (1.95 ml, 14.0 mmol) was added. The mixture was stirred at room temperature for 2 days, washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAc:80% cyclohexane) to yield the title compound (1.13 g, 80%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customazeotroped with toluene
  4. dissolutionThe residue was redissolved in dichloromethane (25 ml)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAc:80% cyclohexane)

Sources & evidence

ORD record
ord-ffb5cbdcdbbb4c54906964b5978df2d6
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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