Sodium Hydroxide → HCID 22252238, compound

HRID 1611962Notes

Reaction equation

HRID 1611962 reaction equation
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:16][O:15][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([NH2:14])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23593643HCID 23593643, compound

Product 1

HCID 22252238HCID 22252238, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 100 mg (0.42 mmol) (7-amino-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 15 ml dioxane and 5 ml ethylene glycol was added 15 ml of a 5 N aq. sodium hydroxide solution and the mixture was heated at 100° C. for 4 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (5/95 methanol/dichloromethane, then 10/89/1 methanol/dichloromethane/triethylamine) followed by trituration in ether afforded 15 mg (20%) 4-methoxy-benzooxazole-2,7-diamine as a brown solid. ES-MS m/e (%): 180 (M+H+, 100).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8727766e06d747d6b578d8ed5c841459
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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