Dichloromethane → HCID 44548376, compound

HRID 1951589Notes

Reaction equation

HRID 1951589 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[O:10][C:11]=2[C:12]([F:15])([F:14])[F:13])=[CH:3][CH:2]=1.ClCCl.[Cl:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>N1C=CC=CC=1>[Cl:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:9]2[O:10][C:11]([C:12]([F:15])([F:13])[F:14])=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[N:8]=2)=[CH:17][CH:18]=1)=[O:30]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 691102-Chlorobenzoyl chlorideHCID 57465378HCID 57465378, compound

Product 1

HCID 44548376HCID 44548376, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

to a stirred mixture of 4-(4-(pyridin-4-yl)-5-(trifluoromethyl)oxazol-2-yl)benzenamine (214 mg, 701 mop and pyridine, anhydrous (0.567 ml, 7011 μmol) in dichloromethane (5.00 ml, 77709 μmol) at room temperature was added 2-chlorobenzoyl chloride (0.0979 ml, 771 μmol) all at once by metered pipet. The reaction was stirred for an hour then concentrated under reduced pressure, taken up in heptane and concentrated under reduced pressure again. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic separation was dried over magnesium sulfate, filtered and filtrate concentrated under reduced pressure to afford a colorless solid. ESI+ m/z=444.1 [MH]+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure again
  3. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  4. customThe organic separation
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationfiltrate concentrated under reduced pressure
  8. customto afford a colorless solid

Sources & evidence

ORD record
ord-3f45aaa3ee2e404cad6f014ef34b2bb1
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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