Thionyl Chloride → HCID 131724951, compound

HRID 2183528Notes

Reaction equation

HRID 2183528 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3=[N:19][N:20]=[C:21]([C:22]4[CH:26]=[C:25]([CH3:27])[O:24][N:23]=4)[N:11]3[N:10]=2)=[N:5][C:4]([CH2:28]O)=[N:3]1.S(Cl)([Cl:32])=O>ClCCl>[Cl:32][CH2:28][C:4]1[N:5]=[C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3=[N:19][N:20]=[C:21]([C:22]4[CH:26]=[C:25]([CH3:27])[O:24][N:23]=4)[N:11]3[N:10]=2)[N:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131724952HCID 131724952, compound

Product 1

HCID 131724951HCID 131724951, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of [1-methyl-5-({[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yl]oxy}methyl]-1H-[1,2,4]triazol-3-yl}methanol (350 mg, 0.9 mmol) in dichloromethane (15 ml) was treated portionwise with thionyl chloride (5 ml) at room temperature for 1 h. The mixture was evaporated in vacuo and the residue partitioned between 5% MeOH/DCM and water. The aqueous layer was basified with saturated K2CO3 solution. The organic layer was separated, dried (MgSO4), and concentrated to give the title compound as a white solid (0.28 g, 78%).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue partitioned between 5% MeOH/DCM and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-366e17feae294e3c9e6d59386f01a69a
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

Loading…