Methyl iodide → HCID 12666070, compound

HRID 848585Notes

Reaction equation

HRID 848585 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][NH:8][C:7](=[S:16])[C:6]=2[CH:17]=1.[OH-].[Na+].[CH3:20]I>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([S:16][CH3:20])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 12666069HCID 12666069, compound

Product 1

HCID 12666070HCID 12666070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ice cold, stirred mixture of 8-chloro-4,5-dihydro-1-methyl-6H-s-triazolo[4,3-a][1,4]benzodiazepine-6-thione (VIIIa) (13.2 g., 0.05 mole) in methanol (75 ml.) was treated with 55 ml. of 0.945 N aqueous sodium hydroxide solution. The ice bath was removed and after 10 minutes methyl iodide (3.11 ml., 0.05 mole) was added to the solution. About 5 minutes after this addition the mixture solidified. It was kept at ambient temperature for one hour, mixed with ice water and stirred for 10 minutes. The solid was collected by filtration, washed with water and dried to give 12.0 g. of the title compound, IXa, melting point 244°-249°. The analytical sample was recrystallized from methylene chloride/ethyl acetate and had melting point 247.5°-249°.

Workup

  1. additionwas treated with 55 ml
  2. additionwas added to the solution
  3. additionAbout 5 minutes after this addition the mixture
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customto give 12.0 g

Sources & evidence

ORD record
ord-5bc4058cf14a4011940a4fd1b374c9b0
Source dataset
uspto-grants-1981_10
Patent number
US04296239

Reaction notes

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