tert-Butanol → 2-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline

HRID 323135

Reaction equation

HRID 323135 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[NH:38][C:41]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 224521542-(Benzyloxy)-4-chlorobenzoic acid

Product 1

HCID 220109632-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Benzyloxy-4-chlorobenzoic acid (3.0 g) was heated under reflux in a mixture of benzene and t-butyl alcohol. Diphenylphosphoryl azide (3.14 g) and triethylamine (1.21 g) were added in one batch to the mixture and reflux was continued for a further 8 hours. Benzene was removed under reduced pressure and the residue taken up in ethyl acetate. An insoluble white solid was removed by filtration. The remaining organic filtrate was washed successively with diluted hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated to give 2-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline (1.6 g).

Workup

  1. temperaturereflux
  2. customBenzene was removed under reduced pressure
  3. customAn insoluble white solid was removed by filtration
  4. washThe remaining organic filtrate was washed successively with diluted hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2e09c12c1f6b4a26b67542010047bcc9
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Linked notes

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