Sodium Hydroxide → HCID 68153471, compound

HRID 1946934Notes

Reaction equation

HRID 1946934 reaction equation
[CH3:1][C:2]1([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH2:7][O:6][CH2:5][C:4](=[O:8])[NH:3]1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1O.[OH-].[Na+]>O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]2[N:18]=[C:12]([C:11]3[CH:10]=[C:9]([C:2]4([CH3:1])[NH:3][C:4](=[O:8])[CH2:5][O:6][CH2:7]4)[CH:17]=[CH:16][CH:15]=3)[O:14][C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 915912-Amino-5-chlorophenolHCID 68153540HCID 68153540, compound

Product 1

HCID 68153471HCID 68153471, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-((RS)-3-methyl-5-oxo-morpholin-3-yl)-benzoic acid (intermediate XXVI-1) (250 mg, 1.1 mmol) and 2-amino-5-chloro-phenol (230 mg, 1.6 mmol) in polyphosphoric acid (1 g) was heated under stirring at 130° C. for 3 hours. For the workup, the reaction mixture was cooled and water was added. The mixture was neutralized with an aqueous solution of sodium hydroxide (10%), then extracted with dichloromethane. The organic layer was dried over sodium sulphate and evaporated to yield the (RS)-5-[3-(6-chloro-benzooxazol-2-yl)-phenyl]-5-methyl-morpholin-3-one (316 mg, 87% of theory) in a quality suited to be engaged in the next step without further purification. MS (ISP): m/z=343 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureFor the workup, the reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-0c9c93216af748afb5bb27e4d7f5be36
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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