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

HRID 1505185Notes

Reaction equation

HRID 1505185 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].O.C[CH2:15][O:16]C(C)=O>>[Cl:8][C:6]1[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]2[O:12][C:15](=[O:16])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 43482942-Amino-4-chloro-6-nitrophenol

Product 1

HCID 299761115-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-oneYield 98%

Procedure

DCI (36.4 mmol, 5.9 g) was added in one portion to 2-amino-4-chloro-6-nitrophenol 5 (5 g, 26.5 mmol) suspended in AcOEt (150 ml) and the reaction was stirred vigorously for 2 hours. 100 ml of water were added to the reaction and then the organic phase was eliminated by evaporation. HCl 20% was added (20 ml) and the resulting solid material was filtered and washed with HCl 1N, cold water, MeOH and ether obtaining 5.6 g of a beige solid. Yield=98% 1HNMR (DMSO, 200 MHz) δ 7.59 (1H, d, J=2.2 Hz), 7.86 (1H, d, J=2.2 Hz), 12.56 (1H, bs)

Workup

  1. customthe organic phase was eliminated by evaporation
  2. additionHCl 20% was added (20 ml)
  3. filtrationthe resulting solid material was filtered
  4. washwashed with HCl 1N, cold water, MeOH and ether obtaining 5.6 g of a beige solid

Sources & evidence

ORD record
ord-70e28a07e29d4e32947a30b27f63cf47
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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