Sodium Hydroxide → HCID 13061977, compound

HRID 1758331Notes

Reaction equation

HRID 1758331 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][CH2:11]Cl)=[N:5][N:4]=[N:3]1.SN1NC[C:18](=[O:21])[C:17]2[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=2[NH:15]1.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][S:7][C:6]2[NH:5][NH:4][C:18](=[O:21])[C:17]3[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=3[N:15]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20509846HCID 20509846, compoundHCID 20509863HCID 20509863, compound

Product 1

HCID 13061977HCID 13061977, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methyl-5-(4-chlorobutyl)thio-1,2,3,4-tetrazole (2.00 g) and 2-mercapto-3H,4H-benzotriazepin-5-one (2.2 g) are dissolved in methanol (50 ml), and thereto is added sodium hydroxide (4.8 g), and the mixture is refluxed at 2.5 hours. After the solvent is distilled off, water is added to the residue, and the mixture is extracted with chloroform. The chloroform layer is washed with 5% aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over magnesium sulfate. After chloroform is distilled off, the residue is recrystallized from methanol to give 1-methyl-5-[4-(3H,4H-1,3,4-benzotriazepin-5-on-2-yl)thiobutyl]thio-1,2,3,4-tetrazole (2.4 g) as colorless prisms, m.p. 94°-95° C.

Workup

  1. temperaturethe mixture is refluxed at 2.5 hours
  2. distillationAfter the solvent is distilled off
  3. additionwater is added to the residue
  4. extractionthe mixture is extracted with chloroform
  5. washThe chloroform layer is washed with 5% aqueous sodium hydroxide and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationAfter chloroform is distilled off
  8. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-20e994ae90c04d4bbb7faa901a88704f
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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