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Sodium Hydroxide → 4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid

HRID 1360231
Notes
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Reaction equation

HRID 1360231 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][N:10]([S:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[O:24][CH3:25])(=[O:16])=[O:15])[C:9]=2[CH:26]=1)=[O:4].[OH-].[Na+]>O1CCCC1.CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([O:24][CH3:25])=[C:17]([S:14]([N:10]2[C:9]3[CH:26]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=3[O:13][CH2:12][CH2:11]2)(=[O:15])=[O:16])[CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 667888284-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester

Product 1

HCID 667885314-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
45 °C

Procedure

A solution of 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester (7.1 g, 17.8 mmol) in tetrahydrofuran (100 mL) and methanol (50 mL) was treated with 3N NaOH (25 mL, 75 mmol, 4.2 equiv.). The mixture was stirred at 45° C. for 1.5 hours. The organic solvents were then removed and the residue acidified with HCl 3N (25 mL). The white precipitate which formed was filtered, washing with water, and dried under high vacuum. 4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid was obtained as a white solid, 6.79 g (99%), MS (ISP): m/e=382.0 (M−H), which was used crude in the following reaction.

Workup

  1. customThe organic solvents were then removed
  2. customThe white precipitate which formed
  3. filtrationwas filtered
  4. washwashing with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-94fa7dd39ea64d34a17ec4dbf039b042
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879845B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes