O-Toluidine → HCID 18630160, compound

HRID 610917Notes

Reaction equation

HRID 610917 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[CH3:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].C(N(CC)CC)C>CN(C=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4]([NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[CH3:19])=[O:6]

Participants

7

Reactant 4

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 18630238HCID 18630238, compound

Product 1

HCID 18630160HCID 18630160, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

The compound of Example c (0.0035 mol, 0.95 g), 15 mL thionyl chloride, and 1 drop of DMF were combined and stirred at RT overnight. Toluene (50 mL) was added and the mixture concentrated to dryness. This process was repeated three times, and the residue dissolved in CH2Cl2 (50 mL). 2-Methylaniline (0.0035 mol, 0.37 g) and triethylamine (0.0035 mol, 0.39 g) were added and the mixture was stirred at RT overnight. The mixture was washed with 10% HCl and twice with water; dried (MgSO4) and concentrated. The title compound was recrystallized from hexanes as a tan solid in 71% yield. m.p. 113-115° C.

Workup

  1. concentrationthe mixture concentrated to dryness
  2. dissolutionthe residue dissolved in CH2Cl2 (50 mL)
  3. stirringthe mixture was stirred at RT overnight
  4. washThe mixture was washed with 10% HCl and twice with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe title compound was recrystallized from hexanes as a tan solid in 71% yield

Sources & evidence

ORD record
ord-04693836a32b43559130cd4fd99d7ae4
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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