Dimethylformamide → 1,10-Decanediyl dianthranilate

HRID 432527

Reaction equation

[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18]C(=O)[O:16][C:14]2=O.[N:25]12[CH2:32][CH2:31]N(CC1)CC2.CN(C)[CH:35]=[O:36]>O.CO>[C:35]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:14](=[O:16])[C:13]1[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:18])(=[O:36])[C:4]1[C:32](=[CH:31][CH:1]=[CH:2][CH:3]=1)[NH2:25]

Participants

Conditions

Temperature: 120 °C

Procedure

1,10-Decanediol (174 grams, 1.0 mol), isatoic anhydride (367 g, 2.25 mol; obtained from Sigma-Aldrich), 1,4-diazabicyclo[2.2.2]octane (22.4 grams, 0.20 mol), and dimethyl formamide (500 milliliters) were combined in 2 liter beaker and the resulting mixture was heated at 120° C. for 1 hour. The mixture was then cooled to room temperature and was treated first with methanol (1,500 milliliters) and then with water (500 milliliters). The solution turned cloudy, and then formed crystals. The crystal suspension was stirred for 2 hours at room temperature, and then was filtered. The solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water, and then was dried to give 1,10-decanediyl dianthranilate as a light beige solid (119 grams, 29 percent yield). The product was adjudged to be highly pure (greater than 98 percent) by 1H-NMR. The melting point of this product as measured by Differential Scanning Calorimetry was 77° C.

Workup

temperatureThe mixture was then cooled to room temperature
customformed crystals
filtrationwas filtered
washThe solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water
customwas dried

Sources & evidence

ORD record: ord-5abfb99d1b454e46894eaadc8887fe9a
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06663703B1

Linked notes

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