O-Toluidine → HCID 18630160, compound

HRID 2188105Notes

Reaction equation

HRID 2188105 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-ffd90ca9dacd404bb97e272dfc7f89ec
Source dataset
uspto-grants-2002_06
Patent number
US06410558B1

Reaction notes

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