2-Methoxyethanol → HCID 178485599, compound

HRID 1977503Notes

Reaction equation

C1(S([C:10](=[CH:15][C:16]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=2)[C:11]([NH:13][CH3:14])=[O:12])(=O)=O)C=CC=CC=1.COCCO.[N-:36]=[N+:37]=[N-:38].[Na+]>O>[CH3:30][C:27]([C:18]1[CH:17]=[C:16]([C:15]2[NH:36][N:37]=[N:38][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[CH:21]=[C:20]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:19]=1[OH:26])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 105 °C

Procedure

A 250 mL 3-neck round-bottom flask immersed in an oil bath, equipped with a mechanical stirrer, thermometer, reflux condenser and nitrogen bubbler, was charged with 42.96 g (0.100 mol) of 2-(benzenesulfonyl)-3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-N-methylacrylamide (II), 100 mL of 2-methoxyethanol and 6.83 g (0.105 mol) of sodium azide. The yellow mixture was heated at 105° C. for 30 h. The cooled orange solution was poured onto a mixture of 150 g of ice and 150 mL of deionized water. The yellow suspension was agitated for 1 h at 5° C. The resulting solid precipitate was filtered off and washed with 5×50 mL of cold deionized water. The recovered solids were dried in vacuo over potassium hydroxide flakes to afford yellow solids, 30.2 g of crude product (I), 98.7% purity by HPLC.

Workup

customA 250 mL 3-neck round-bottom flask immersed in an oil bath
customequipped with a mechanical stirrer
temperaturethermometer, reflux condenser
filtrationThe resulting solid precipitate was filtered off
washwashed with 5×50 mL
dry with materialThe recovered solids were dried in vacuo over potassium hydroxide flakes

Sources & evidence

ORD record: ord-f6e174578b4848cb933dfbc32d2bf006
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232471B1

Reaction notes

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