Benzaldehyde dimethyl acetal → 3-(5-Chloro-2-methoxy-benzenesulfonyl)-2-phenyl-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester

HRID 641308Notes

Reaction equation

HRID 641308 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:14])=[O:13])[CH:5]=1.CO[CH:27](OC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCCCCCC>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:11]([S:12]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[O:22][CH3:23])(=[O:13])=[O:14])[C:6]=2[CH:5]=1)=[O:24]

Participants

5

Reactant 3

HCID 62375Benzaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrateHCID 667891293-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 667889833-(5-Chloro-2-methoxy-benzenesulfonyl)-2-phenyl-2,3-dihydro-benzooxazole-5-carboxylic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester (example 30, step 1; 200 mg, 0.537 mmol), benzaldehyde dimethyl acetal (0.5 mL) and toluene-4 sulfonic acid monohydrate (10 mg, 54 μmol) was stirred at 100° C. for 48 h. After cooling, heptane was added, and the precipitate was collected by filtration to afford 3-(5-chloro-2-methoxy-benzenesulfonyl)-2-phenyl-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester (208 mg, 84%). Light yellow solid, MS (ISP)=460.2 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-dd3dba9a10df4eb6ac5167ce746e4efa
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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