Sulfuryl chloride → HCID 89876162, compound

HRID 2169771Notes

Reaction equation

HRID 2169771 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[N:7][N:6]([CH3:10])[C:5](=[O:11])[C:4]=1[N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH3:21].S(Cl)([Cl:25])(=O)=O>C(Cl)Cl>[Cl:25][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([C:4]2[C:5](=[O:11])[N:6]([CH3:10])[N:7]=[C:8]([CH3:9])[C:3]=2[O:2][CH3:1])[C:13]=1[CH3:21]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 117833139HCID 117833139, compound

Product 1

HCID 89876162HCID 89876162, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 5-methoxy-2,6-dimethyl-4-(2-methylindol-1-yl)pyridazin-3-one (147 mg, 0.52 mmol) in DCM (3 ml) at 0° C., was added dropwise a solution of sulfuryl chloride (70 mg, 0.52 mmol) in DCM (1 ml). Further DCM (1 ml) was added. After a reaction time of 1 h, the mixture was quenched by addition of sat. aqueous NaHCO3 (2 ml). The resulting mixture was filtered through solid MgSO4, washing with DCM. The filtration liquors were concentrated in vacuo to afford the title compound as a pale brown solid (158 mg, 96%). The material was used for subsequent reactions without further purification.

Workup

  1. customAfter a reaction time of 1 h, the mixture was quenched by addition of sat. aqueous NaHCO3 (2 ml)
  2. filtrationThe resulting mixture was filtered through solid MgSO4
  3. washwashing with DCM
  4. filtrationThe filtration liquors
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-b16d69cba5da42d58c4203ede71ae446
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

Loading…