Ammonium Acetate → HCID 22312927, compound

HRID 351568Notes

Reaction equation

HRID 351568 reaction equation
[NH4+:1].C([O-])(=O)C.[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[C:21]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)([CH3:25])[C:22](Cl)=[O:23]>CC(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[C:21]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)([CH3:25])[C:22]([NH2:1])=[O:23]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 22312914HCID 22312914, compound

Product 1

HCID 22312927HCID 22312927, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetic acid, ammonium salt (3 g) was added at RT to a solution of (±)-2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α-methylbenzeneacetyl chloride (0.007 mol) in 2-propanone (30 ml). The mixture was stirred at RT for 5 hours. Acetic acid, ammonium salt was filtered off and the solvent was evaporated. The residue was taken up in CH2Cl2, washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 1.6 g (57%) of (±)-2-chloro-a-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α-methylbenzeneacetamide (comp. 1.18).

Workup

  1. filtrationAcetic acid, ammonium salt was filtered off
  2. customthe solvent was evaporated
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bb33951d9a8c4a6cb46fb228d2029a77
Source dataset
uspto-grants-2004_06
Patent number
US06743792B2

Reaction notes

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