1,1'-Carbonyldiimidazole → 2(3H)-Benzoxazolone,4-fluoro-(9CI)

HRID 1991334Notes

Reaction equation

HRID 1991334 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[OH:21]>C1COCC1.C(OCC)(=O)C>[F:20][C:19]1[C:14]2[NH:13][C:1](=[O:2])[O:21][C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 27827782-amino-3-fluorophenol

Product 1

HCID 450905562(3H)-Benzoxazolone,4-fluoro-(9CI)

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

1,1′-Carbonyldiimidazole (11.4 g, 0.0703 mol) is added portionwise to a solution of 2-amino-3-fluorophenol (Step 3, 8.94 g, 0.0703 mol) in THF (200 ml) and warmed at 60° C. for 2 h. The reaction mixture is diluted with ethyl acetate (200 ml), washed with 2N HCl and saline, dried (MgSO4), and evaporated to give product as a white solid suitable for use in the next step (10.6 g, 99%); mp 131-3° C.

Workup

  1. washwashed with 2N HCl and saline
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give product as a white solid suitable for use in the next step (10.6 g, 99%)

Sources & evidence

ORD record
ord-e1a8a49e3c80472bb506bfd00d9ed2c2
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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