Methyl iodide → HCID 18707479, compound

HRID 1741155Notes

Reaction equation

HRID 1741155 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[S:15][C:14](=[S:16])[NH:13][N:12]=1.[OH-].[Na+].I[CH3:20]>CO>[CH3:20][S:16][C:14]1[S:15][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[N:12][N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 14278808HCID 14278808, compound

Product 1

HCID 18707479HCID 18707479, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-naphthalen-2-yl-3H-[1,3,4]thiadiazole-2-thione (2.8 g, 11.5 mmol) in methanol (100 ml) was added dropwise 1 N sodium hydroxide (12 ml, 12 mmol) at 0° C. After stirred for 10 min. at 0° C. iodomethane (2.0 g, 13.8 mmol) was added dropwise and stirring was continued at 0° C. for 5 min. and at room temperature for 2 h. The volatiles were evaporated in vacuo and to the residue was added water (100 ml). The precipitate was filtered off and dried in vacuo at 50° C. The dried compound (2.4 g) was recrystallised from ethyl acetate (60 ml) affording after drying in vacuo at 50° C. 0.7 g (23%) of the title compound as a solid.

Workup

  1. additionwas added dropwise
  2. customThe volatiles were evaporated in vacuo and to the residue
  3. additionwas added water (100 ml)
  4. filtrationThe precipitate was filtered off
  5. customdried in vacuo at 50° C
  6. customThe dried compound (2.4 g) was recrystallised from ethyl acetate (60 ml)
  7. customaffording
  8. customafter drying in vacuo at 50° C

Sources & evidence

ORD record
ord-9d9c29c4866e4f55bb2b4c3cad915cf9
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

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