Methanol → Stearyl anthranilate

HRID 1357322Notes

Reaction equation

HRID 1357322 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.CO>CN(C)C=O>[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 887MethanolHCID 8221Stearyl AlcoholHCID 8359Isatoic AnhydrideHCID 9237Dabco

Product 1

HCID 12081288Stearyl anthranilateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of octadecanol (270 grams, 1.0 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.), isatoic anhydride (244 grams, 1.5 mol; obtained from Sigma-Aldrich Co.), and 1,4-diazabicyclo[2.2.2]octane (56 grams, 0.50 mol; obtained from Sigma-Aldrich Co.) in 1,000 milliliters of dimethylformamide was stirred and heated to 100° C. in a 4 liter beaker. Vigorous gas evolution occurred. After 10 minutes, the resultant brown solution was heated to 150° C. for 15 minutes. The reaction mixture was then cooled to 50° C. and vigorously stirred while 3,000 milliliters of methanol was added. The resultant suspension was stirred for 0.5 hour followed by vacuum filtration. The solid thus obtained was washed in the filter funnel with 4×300 milliliter portions of methanol and then dried in air to give the product stearyl anthranilate as white powder (330.5 grams, 85 percent yield).

Workup

  1. temperaturethe resultant brown solution was heated to 150° C. for 15 minutes
  2. temperatureThe reaction mixture was then cooled to 50° C.
  3. additionwas added
  4. filtrationfollowed by vacuum filtration
  5. customThe solid thus obtained
  6. washwas washed in the filter funnel with 4×300 milliliter portions of methanol
  7. customdried in air

Sources & evidence

ORD record
ord-f33fc25bf8d8486189de536aae93495b
Source dataset
uspto-grants-2003_07
Patent number
US06590082B1

Reaction notes

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