Dimethylformamide → Stearyl anthranilate

HRID 130267

Reaction equation

HRID 130267 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]12[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:25]C(=O)O[C:21]2=[O:22].N12CCN(CC1)CC2.CN(C)C=O>CO>[C:21]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:22])[C:20]1[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH2:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8221Stearyl AlcoholHCID 8359Isatoic AnhydrideHCID 9237Dabco

Product 1

HCID 12081288Stearyl anthranilateYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Into a 4 liter beaker equipped with magnetic stirrer, dropping funnel, and thermometer, was charged stearyl alcohol (270.0 grams, 1.0 mol; obtained from Sigma-Aldrich), isatoic anhydride (244.0 grams, 1.5 mol), 1,4-diazabicyclo(2.2.2)octane (DABCO) (56 grams, 0.5 mol), and dimethylformamide (750 milliliters). The mixture was stirred and heated to 120° C. for a period of about 2 hours. The mixture was then cooled to 50° C., and methanol (3 liters) was added. A thick white precipitate formed, which was filtered and then washed with 3×1 liter portions of methanol and oven dried at 60° C. to yield 295.8 grams of a beige solid at 76 percent yield.

Workup

  1. customInto a 4 liter beaker equipped with magnetic stirrer
  2. temperatureThe mixture was then cooled to 50° C.
  3. customA thick white precipitate formed
  4. filtrationwhich was filtered
  5. washwashed with 3×1 liter portions of methanol and oven
  6. customdried at 60° C.

Sources & evidence

ORD record
ord-dd2ffcd1a88f49b38c951d7c4ce09a70
Source dataset
uspto-grants-2008_06
Patent number
US07381253B2

Linked notes

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