Chlorzoxazone → HCID 53767114, compound

HRID 2298564Notes

Reaction equation

HRID 2298564 reaction equation
[CH:1]1[C:6](Cl)=[CH:5][C:4]2[NH:8][C:9]([O:11][C:3]=2[CH:2]=1)=[O:10].[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]=[CH2:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(#N)C>[C:12]([O:16][C:17]([NH:19][CH2:20][CH:21]=[CH:22][C:6]1[CH:1]=[CH:2][C:3]2[O:11][C:9](=[O:10])[NH:8][C:4]=2[CH:5]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 2733ChlorzoxazoneHCID 80271Tri-o-tolylphosphineHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 53767114HCID 53767114, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of chlorzoxazone, 3-(t-butoxycarbonylamino)-1-propene, palladium diacetate, tritolylphosphine, and acetonitrile is cooled to −78° C., degassed, and sealed in a reaction tube. The mixture is kept at 50° C. with stirring for 60 hours, then cooled and opened and the acetonitrile removed under vacuum. The residue is dissolved in ethyl acetate and washed successively with 5% aqueous NaHCO3 and brine. After drying over Mg2SO4, the mixture is filtered and evaporated. Silica gel chromatography gives 5-(3-(t-butoxycarbonylamino)-1-propenyl)-2-benzoxazolone.

Workup

  1. customdegassed
  2. customsealed in a reaction tube
  3. customis kept at 50° C.
  4. temperaturecooled
  5. customthe acetonitrile removed under vacuum
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed successively with 5% aqueous NaHCO3 and brine
  8. dry with materialAfter drying over Mg2SO4
  9. filtrationthe mixture is filtered
  10. customevaporated

Sources & evidence

ORD record
ord-0cfa68b54f4045a2b12b1856665cbb71
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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