Ammonium Acetate → HCID 22312927, compound

HRID 965642Notes

Reaction equation

HRID 965642 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-α-(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-b31c58c587234a2e9b2b0b3bebb504f8
Source dataset
uspto-grants-2005_10
Patent number
US06951857B2

Reaction notes

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