2-Chlorobenzylamine → 2-(2-Chloro-benzylamino)-benzooxazol-6-ol

HRID 1988398Notes

Reaction equation

HRID 1988398 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH:16][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 666482-ChlorobenzylamineHCID 234412462-Chloro-1,3-benzoxazol-6-OL

Product 1

HCID 577253862-(2-Chloro-benzylamino)-benzooxazol-6-ol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Chloro-benzooxazol-6-ol (1 eq) and 2-chloro-benzylamine (2 eq) was dissolved in NMP. Using a Personal Chemistry microwave system, the mixture was reacted at 180° C. for six minutes. The crude reaction mixture was diluted with ethyl acetate and washed once with brine and once with 1N HCl, or washed twice with brine, depending on the amine used. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. This material was purified by silica gel column using hexane and ethyl acetate. MH+=275.1.

Workup

  1. customthe mixture was reacted at 180° C. for six minutes
  2. customThe crude reaction mixture
  3. washwashed once with brine and once with 1N HCl
  4. washwashed twice with brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis material was purified by silica gel column

Sources & evidence

ORD record
ord-a44c1871b5a94442b3ebb8fae14c4471
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

Loading…