Dichloroacetic Acid → HCID 20067568, compound

HRID 982352Notes

Reaction equation

HRID 982352 reaction equation
C([O-])(=O)C.[Na+].ClC(Cl)C(O)=O.Cl.[NH2:13][OH:14].O[C:16]1([CH3:35])[C:22]2[CH:23]=[CH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:21]=2[CH:20]=[CH:19][C:18]2[CH:31]=[CH:32][CH:33]=[CH:34][C:17]1=2>ClCCl>[OH:14][NH:13][C:16]1([CH3:35])[C:22]2[CH:23]=[CH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:21]=2[CH:20]=[CH:19][C:18]2[CH:31]=[CH:32][CH:33]=[CH:34][C:17]1=2

Participants

6

Reactant 4

HCID 6597Dichloroacetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20067590HCID 20067590, compound

Product 1

HCID 20067568HCID 20067568, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium acetate (5.7 g) and dichloroacetic acid (8.5 ml) were stirred together in dichloromethane (8.5 ml) at 0° C. for 5 minutes then hydroxylamine hydrochloride (4.8 g) added. After 1 h at room temperature more dichloromethane (17 ml) was added and after a further 30 minutes, the product from Example 7. Step A (1.9q) was added. After 1 h at room temperature the reaction mixture was poured into ice-water (200 ml) and washed with ammonia solution (70 ml). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the required product (2.04 g) as a colourless form. Spectral data were consistent with the proposed structure.

Workup

  1. washwashed with ammonia solution (70 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab0874b2284748ba90f6f75ad646754a
Source dataset
uspto-grants-1991_02
Patent number
US04996211

Reaction notes

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