Ethyl 2-methoxyacetate → Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

HRID 17367

Reaction equation

HRID 17367 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18].CO[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CCCCCC>[CH2:25]([O:24][C:22]([C:21]1[O:8][C:7]2[C:6]([F:9])=[C:5]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]([CH3:16])=[C:3]([C:17]#[N:18])[C:2]=2[N:1]=1)=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 77544Ethyl 2-methoxyacetateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (5.0 g, 20.64 mmol) and ethyl methoxyacetate (18.18 g, 82.56 mmol) were stirred at 100° C. for 23 hours under nitrogen atmosphere. The reaction liquid was cooled to room temperature, and left at the same temperature for 17 hours. At 0° C., hexane was added to the suspension, and left at the same temperature for 1 hour. With washing with hexane, the precipitated crystal was collected by filtration. The crystal was collected, dried at 50° C. under reduced pressure for 4 hours, and then at room temperature for 12 hours to obtain the entitled compound (6.39 g, 96%) as a pale brown powder.

Workup

  1. customThe reaction liquid
  2. waitleft at the same temperature for 1 hour
  3. washWith washing with hexane
  4. filtrationthe precipitated crystal was collected by filtration
  5. customThe crystal was collected
  6. customdried at 50° C. under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-59785a76fe4444ebbfba8c01f827d571
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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