1,1'-Carbonyldiimidazole → N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide

HRID 1481691Notes

Reaction equation

HRID 1481691 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:31][NH:32][O:33][CH3:34].Cl>C(Cl)Cl>[CH3:34][O:33][N:32]([CH3:31])[C:16]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][C:9]=2[CH:15]=1)=[O:18]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 109007142-Phenyl-1,3-benzoxazole-6-carboxylic acid

Product 1

HCID 89421776N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-phenylbenzo[d]oxazole-6-carboxylic acid (2.0 g, ca. 8.4 mmol) in CH2Cl2 was added CDI (1.6 g, 9.9 mmol, 1.2 eq) at 0° C. The reaction was warmed to room temperature then stirred for 1 h to give a homogeneous solution. The mixture was cooled to 0° C. before MeNHOMe-HCl (0.98 g, 10.0 mmol, 1.2 eq) was added. After 12 h, the reaction was quenched with H2O and extracted with CH2Cl2 (3×50 mL). Solvent was removed then crude product was purified by flash column chromatography (0-25% EtOAc in hexanes) to afford N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide (1.57 g, 5.6 mmol, 67% over two steps).

Workup

  1. customto give a homogeneous solution
  2. additionwas added
  3. waitAfter 12 h
  4. customthe reaction was quenched with H2O
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. customSolvent was removed
  7. customcrude product was purified by flash column chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dc54bf1a35d34c928fb1907d9443cc51
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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