Water → HCID 19872290, compound

HRID 477743Notes

Reaction equation

HRID 477743 reaction equation
C(S[C:9]1[N:13]=[C:12]([CH3:14])[N:11]([C:15]2[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][CH3:24])[N:16]=2)[N:10]=1)C1C=CC=CC=1.O.[S:26]([Cl:30])(Cl)(=[O:28])=[O:27]>ClCCl>[CH3:22][O:21][C:19]1[N:18]=[C:17]([O:23][CH3:24])[N:16]=[C:15]([N:11]2[C:12]([CH3:14])=[N:13][C:9]([S:26]([Cl:30])(=[O:28])=[O:27])=[N:10]2)[N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 19872286HCID 19872286, compound

Product 1

HCID 19872290HCID 19872290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 3-benzylthio-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-5-methyl-1,2,4-triazole (6 g) in dichloromethane (60 ml) was treated with silica gel (14 g) 60-120 mesh and water (2.8 g). Sulphuryl chloride (10.6 ml) in dichloromethane (12 ml) was added dropwise with stirring whilst maintaining a temperature of 5° C. for 2 hours. The silica gel was filtered off, washed with dichloromethane (150 ml) and ethyl acetate (100 ml), and the combined washings were extracted with water and aqueous sodium bicarbonate. The organic layer was dried and evaporated at 40° C. in vacuo. The residue was triturated with ether and filtered to give 3 g of the desired product.

Workup

  1. filtrationThe silica gel was filtered off
  2. washwashed with dichloromethane (150 ml) and ethyl acetate (100 ml)
  3. extractionthe combined washings were extracted with water and aqueous sodium bicarbonate
  4. customThe organic layer was dried
  5. customevaporated at 40° C. in vacuo
  6. customThe residue was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-27b871569aae42839d837808bc48df34
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

Loading…