Methyl iodide → HCID 86733573, compound

HRID 1658534Notes

Reaction equation

HRID 1658534 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2=[N:15][N:16]([CH3:18])[CH2:17][N:13]2[C:12]2[S:19](=[O:22])[CH2:20][CH2:21][C:11]=2[CH2:10][N:9]=1.[H-].[Na+].[CH3:25]I>CN(C)C=O.CCOCC>[CH3:25][CH:20]1[S:19](=[O:22])[C:12]2[N:13]3[CH2:17][N:16]([CH3:18])[N:15]=[C:14]3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][CH2:10][C:11]=2[CH2:21]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21527853HCID 21527853, compound

Product 1

HCID 86733573HCID 86733573, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1 g of 6-o-chlorophenyl-8-methyl-1,2-dihydro-4H-s-triazolo[3,4-c]-thieno[2,3-e][1,4]diazepin-1-one is dissolved in 25 ml of dimethylformamide, and 0.09 g of sodium hydride (50% in mineral oil) is added, and the resulting mixture is heated at 60° C on a water bath with stirring for 30 minutes. After cooling to room temperature, a solution of 0.6 g of methyl iodide in 5 ml of ether is added dropwise, and the whole mixture is stirred at room temperature for 7 hours. Then the reaction mixture is poured into ice water, the precipitated crystals are filtered off, and the filtrate is extracted with chloroform. The extract is washed with water, dried over anhydrous magnesium sulfate, and the chloroform is removed under reduced pressure. The residue is recrystallized from a mixture of ligroin and ethanol to give the title compound as white crystals, melting at 199°-200° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe whole mixture is stirred at room temperature for 7 hours
  3. filtrationthe precipitated crystals are filtered off
  4. extractionthe filtrate is extracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe chloroform is removed under reduced pressure
  8. customThe residue is recrystallized from a mixture of ligroin and ethanol

Sources & evidence

ORD record
ord-5e8122e91a2f4a098a09e4bfa4a1a29b
Source dataset
uspto-grants-1976_06
Patent number
US03965111

Reaction notes

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