Dimethyl Sulfide → N-(4-methoxybenzyl)-2-(methoxymethyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528647Notes

Reaction equation

HRID 528647 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][C:19](=O)[CH:18]([CH2:22][O:23][CH3:24])[O:17][C:16]=3[CH:25]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CSC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH:18]([CH2:22][O:23][CH3:24])[O:17][C:16]=3[CH:25]=2)(=[O:11])=[O:10])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 89761918N-(4-methoxybenzyl)-2-(methoxymethyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 89761839N-(4-methoxybenzyl)-2-(methoxymethyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamideYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-2-(methoxymethyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (500 mg, 1.05 mmol) in THF (10 mL) was added BH3.DMS (0.15 mL, 1.57 mmol, Aldrich) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h. After completion, the reaction mixture was quenched with methanol (7 mL) and was azeotroped with methanol (3×15 mL). The solvent was removed under reduced pressure and the crude material thus obtained was purified by column chromatography (silica: 100-200; elution: 30% ethyl acetate in hexane) to get pure N-(4-methoxybenzyl)-2-(methoxymethyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (350 mg, 71.6%) as a brown solid. m/z (ESI) 462.2 (M+H)+.

Workup

  1. customat 0° C
  2. customAfter completion, the reaction mixture was quenched with methanol (7 mL)
  3. customwas azeotroped with methanol (3×15 mL)
  4. customThe solvent was removed under reduced pressure
  5. customthe crude material thus obtained
  6. customwas purified by column chromatography (silica: 100-200; elution: 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-90803820311b4f3a9de4f956027387d6
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

Loading…