5-Chloro-2-methoxybenzene-1-sulfonyl chloride → 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester

HRID 1660780Notes

Reaction equation

HRID 1660780 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:14][O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][CH2:25][CH2:24][NH:23][C:22]=2[CH:27]=1)=[O:17]>ClCCl.N1C=CC=CC=1>[CH3:14][O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][CH2:25][CH2:24][N:23]([S:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:12][CH3:13])(=[O:10])=[O:9])[C:22]=2[CH:27]=1)=[O:17]

Participants

5

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 16244461methyl 3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Product 1

HCID 667888284-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-chloro-2-methoxy-benzenesulfonyl chloride (4.7 g, 19.7 mmol, 1.05 equiv.) in dichloromethane (60 mL) and pyridine (25 mL) was added a solution of 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester (3.6 g, 18.8 mmol, 1 equiv.) in dichloromethane (60 mL). The mixture was stirred at room temperature overnight then the solvent was removed. The residue was purified by flash chromatography to yield 4-(5-chloro-2-methoxybenzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester as a pink solid, 7.12 g (95%), MS (ISP): m/e=398.0 (M+H+.); δH (300 MHz; CDCl3) 8.24 (1H, s), 8.07 (1H, s), 7.72 (1H, dd), 7.48 (1H, dd), 6.91 (1H, d), 6.89 (1H, d), 4.10 (2H, m), 3.91 (2H, m), 3.88 (3H, s), 3.63 (3H, s).

Workup

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-769bf648737c416dbc943bbbd02a2e60
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

Loading…