Acetone → HCID 131711713, compound

HRID 2052666Notes

Reaction equation

[CH:1]1([NH:7][S:8]([C:11]2[CH:12]=[C:13]([C:21]([OH:23])=O)[C:14]3[O:19][CH2:18][CH2:17][O:16][C:15]=3[CH:20]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.ClC(OC[CH:30]([CH3:32])C)=O.C([NH:35]CC)C.C[C:39]([CH3:41])=O>C(N(CC)CC)C>[CH2:39]([C:20]1[C:15]2[O:16][CH2:17][CH2:18][O:19][C:14]=2[C:13]([C:21]([NH2:35])=[O:23])=[C:12]([CH2:30][CH3:32])[C:11]=1[S:8](=[O:9])(=[O:10])[NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH3:41]

Participants

Conditions

Temperature: 10 °C

Procedure

34.1 g of 7-cyclohexylsulfamoyl-1,4-benzodioxane-5-carboxylic acid, 35 ml of water and 10.5 g of triethylamine were introduced into a 250 ml balloon flask provided with a stirrer and a thermometer. 100 ml of acetone were added and the mixture was cooled to 10° C. 14 g of isobutyl chloroformate were added and the mixture was maintained under stirring for 30 minutes at room temperature. 8 g of diethylamine were introduced at a temperature of from 15°-20° C. After stirring for three hours, the solvent was removed under vacuum. The residue was washed with water, dried, dissolved in 180 ml of absolute ethanol and treated with 3 g of black carbon. After filtration and crystallization, 23 g of diethyl-7-cyclohexylsulfamoyl-1,4-benzodioxane-5-carboxamide were obtained (M.P.: 201° C.). The structure was confirmed by infrared and nuclear magnetic resonance analyses.

Workup

customprovided with a stirrer
temperaturethe mixture was maintained
stirringAfter stirring for three hours
customthe solvent was removed under vacuum
washThe residue was washed with water
customdried
dissolutiondissolved in 180 ml of absolute ethanol
additiontreated with 3 g of black carbon
filtrationAfter filtration and crystallization

Sources & evidence

ORD record: ord-9800b78b210e426393af1f80db6b5059
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04186135

Reaction notes

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