Sulfamic Acid → 4-Difluoromethoxy-8-nitrodibenzo[b,d]furan-1-carboxylic acid

HRID 2039661Notes

Reaction equation

HRID 2039661 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([CH:20]=[O:21])=[CH:6][CH:5]=1.S(=O)(=O)([OH:25])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[F:22][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([C:20]([OH:25])=[O:21])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 211057104-Difluoro methoxy-8-nitro-1-formyl dibenzo[b,d]furanHCID 23668197Sodium Chlorite

Product 1

HCID 211057114-Difluoromethoxy-8-nitrodibenzo[b,d]furan-1-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirring solution of 4-(difluoromethoxy)-8-nitrodibenzo[b,d]furan-1-carbaldehyde (6.5 g, 0.021 mol) and sulphamic acid (3.7 g, 0.038 mol) in acetone (25 mL) was added sodium chlorite (3.0 g, 0.033 mol) in water (25 mL) dropwise at 5-10° C. After 15 minutes, the reaction slurry was allowed to stir at room temperature for 17 hours. The reaction slurry was poured into ice-cold water and filtered. The solid obtained was washed with hexane and dried. Yield—81.9%. 1H-NMR (DMSO-d6) δ: 7.44-7.64-7.80 (t, 2H), 8.09-8.16 (m, 2H), 8.53-8.55 (m, 1H), 9.80 (d, 1H), 13.75 (s, 1H); HPLC (purity): 87.6%; Mass calculated for C14H7F2NO6-323.2, observed—322.0; Rf—0.25 (Ethyl acetate:Hexane (1:1).

Workup

  1. additionThe reaction slurry was poured into ice-cold water
  2. filtrationfiltered
  3. customThe solid obtained
  4. washwas washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-b294362be8dc4d41b677058794d35830
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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