Dimethylformamide → HCID 21443811, compound

HRID 130268Notes

Reaction equation

HRID 130268 reaction equation
[N:1]([CH2:8][CH2:9][OH:10])([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[C:11]12[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH:16]C(=O)[O:14][C:12]2=[O:13].N12CCN(CC1)CC2.CN(C)C=O>O.CO>[C:12]([OH:14])(=[O:13])[C:11]1[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:16].[C:12]([OH:14])(=[O:13])[C:11]1[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:16].[C:12]([OH:14])(=[O:13])[C:11]1[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:16].[N:1]([CH2:8][CH2:9][OH:10])([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7618TriethanolamineHCID 8359Isatoic AnhydrideHCID 9237Dabco

Product 1

HCID 21443811HCID 21443811, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Into a 1 liter round bottom flask-equipped with mechanical stirrer, dropping funnel, and thermometer was charged triethanolamine (149.2 grams, 1.0 mol; obtained from Sigma-Aldrich), isatoic anhydride (520.0 grams, 3.5 mol), 1,4-diazabicyclo(2.2.2)octane (DABCO) (45.0 grams, 0.4 mol), and dimethylformamide (1,500 milliliters). The mixture was stirred and heated to 120° C. for a period of about 2 hours. The mixture was then cooled to room temperature, and methanol (2 liters) was added. Deionized water (1 liter) was added, causing the solution to turn cloudy. This solution was stirred for 2 hours, and then filtered, washed with 5×250 milliliters of methanol, and oven dried at 60° C. to yield 506 grams of a beige solid.

Workup

  1. customInto a 1 liter round bottom flask-equipped with mechanical stirrer
  2. temperatureThe mixture was then cooled to room temperature
  3. stirringThis solution was stirred for 2 hours
  4. filtrationfiltered
  5. washwashed with 5×250 milliliters of methanol, and oven
  6. customdried at 60° C.

Sources & evidence

ORD record
ord-b5ed1c26c437491483a4f7cfde992a85
Source dataset
uspto-grants-2008_06
Patent number
US07381253B2

Reaction notes

Loading…