Diethoxymethane → 7-bromo-1-(5-chloro-2-methoxy-benzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine

HRID 1660858Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:21][OH:22])=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])(=[O:11])=[O:10])[CH:7]=1.O.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCOCC)C>CCCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:21][O:22][CH2:24][N:8]([S:9]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[O:19][CH3:20])(=[O:11])=[O:10])[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxy-benzenesulfonamide (2.51 g, 6.17 mmol), toluene-4-sulfonic acid monohydrate (117 mg, 0.617 mmol), and formaldehyde diethyl acetal (15.5 mL) was heated under reflux at 100° C. for 16 h. After cooling, heptane was added to the suspension, which was stirred for 15 min. The precipitate was collected by filtration and dried to afford 7-bromo-1-(5-chloro-2-methoxy-benzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine (2.25 g, 87%). Off-white solid, MS (ISP)=418.1 (M+H)+.

Workup

temperaturewas heated
temperatureAfter cooling
filtrationThe precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-1a588c4f299b4d4681e491c595cff3ab
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030308B2

Reaction notes

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