Hydrochloric Acid → HCID 22312904, compound

HRID 965641Notes

Reaction equation

HRID 965641 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([CH3:20])[C:17](Cl)=[O:18].[CH3:28][NH2:29].O.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([CH3:20])[C:17]([NH:29][CH3:28])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 6329MethylamineHCID 22312914HCID 22312914, compound

Product 1

HCID 22312904HCID 22312904, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 CH2Cl2 (20 ml) was added at RT to methanamine 40% in water (0.105 mol). The mixture was stirred at RT for 4 hours, then poured out into water, acidified with HCl (3N) and extracted with CH2Cl2. The organic layer was separated, 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 1.25 g (43%) of (±)-2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α,N-dimethylbenzeneacetamide (comp. 1.14).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d0387f0f1695469fb8234a5a1e52165e
Source dataset
uspto-grants-2005_10
Patent number
US06951857B2

Reaction notes

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