Hydrochloric Acid → 5-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 656377Notes

Reaction equation

HRID 656377 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].Cl>C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]2[O:12][C:13](=[O:14])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 43482942-Amino-4-chloro-6-nitrophenol

Product 1

HCID 299761115-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-4-chloro-6-nitrophenol (2.00 g, 10.6 mmol) in THF (50 mL) was added 1,1′-carbonyldiimidazole (2.06 g, 12.7 mmol) and the resulting mixture was stirred at ambient temperature for 1 h. The mixture was poured into 1 N hydrochloric acid and the precipitate was isolated by filtration, washed with H2O, then hexanes, and dried in vacuo to give the title compound.

Workup

  1. customthe precipitate was isolated by filtration
  2. washwashed with H2O
  3. dry with materialhexanes, and dried in vacuo

Sources & evidence

ORD record
ord-71f4f2f31cda40fe89d02f50095d1fb0
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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