Sulfamic Acid → HCID 86607794, compound

HRID 2105832Notes

Reaction equation

HRID 2105832 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])[CH3:2].S(=O)(=O)([OH:19])N.Cl([O-])=O.[Na+]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])[C:11]([OH:19])=[O:12])[CH3:2]

Participants

7

Reactant 3

HCID 5987Sulfamic Acid2×HCID 23668197Sodium ChloriteHCID 86607795HCID 86607795, compound

Product 1

HCID 86607794HCID 86607794, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 2-ethoxy-5-formyl-benzoic acid ethyl ester (1.0 g, 4.5 mmol) in 10 mL of dimethylformamide was added dropwise sulfamic acid (610.4 mg, 6.3 mmol) in 5 mL of water. After addition of sulfamic acid, sodium chlorite (737.2 mg, 8.2 mmol) in 5 mL of water was added dropwise. Reaction was allowed to stir for 2 h at room temperature. Reaction was diluted with brine and extracted with ethyl acetate. Organic extract was dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 4-ethoxy isopthalic acid 3-ethyl ester as a white solid (900 mg, 84%). LC-MS: 239.2 [(M+H)+].

Workup

  1. additionwas added dropwise
  2. customReaction
  3. customReaction
  4. extractionextracted with ethyl acetate
  5. extractionOrganic extract
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8201bee1812408fa275bb75b7c7e7e5
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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