Water → HCID 22312909, compound

HRID 351564Notes

Reaction equation

HRID 351564 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N:17]3[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]3)[C:12]=2[Cl:25])[C:9]#[N:10])=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].Cl[CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36].C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N:17]3[C:22](=[O:23])[N:21]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:20](=[O:24])[CH:19]=[N:18]3)[C:12]=2[Cl:25])[C:9]#[N:10])=[CH:4][C:3]=1[C:26]([F:29])([F:27])[F:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 22312895HCID 22312895, compound

Product 1

HCID 22312909HCID 22312909, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-4-chloro-α-[2-chloro-3-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]-3-(trifluoromethyl)benzeneacetonitrile (0.00542 mol), 1-(chloromethoxy)-2-methoxyethane (0.006 mol) and triethylamine (0.0065 mol) in THF (15 ml) was stirred at RT for 2 hours. The mixture was poured out into water and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 3.4 g of (±)-4-chloro-α-[2-chloro-3-[4,5-dihydro-4-[(2-methoxyethoxy)methyl]-3,5-dioxo-1,2,4-triazin-2(3H)-yl]phenyl]-3-(trifluoromethyl)benzeneacetonitrile (interm. 22).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3c34c69ca80442ce90b70d8acb2dfbbe
Source dataset
uspto-grants-2004_06
Patent number
US06743792B2

Reaction notes

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