Water → HCID 178505113, compound

HRID 866880Notes

Reaction equation

HRID 866880 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[S:13][C:14]1[N:18]([CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[N:17]=[N:16][N:15]=1)([O-])=O.C[O-].[Na+].O>CO>[CH3:25][S:22]([NH:21][CH2:20][CH2:19][N:18]1[C:14]([SH:13])=[N:15][N:16]=[N:17]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 203186985-(2,4-Dinitrophenylthio)-1-(2-methanesulfonamidoethyl)tetrazole

Product 1

HCID 178505113HCID 178505113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,4-Dinitrophenylthio)-1-(2-methanesulfonamidoethyl)tetrazole (4.46 g, 11.5 mmol) was added to 60 ml of 5% sodium methoxide in methanol. After 1 hour, water was added and the solid material was removed by filtration. The filtrate was concentrated in vacuo and 3N hydrochloric acid was added to the residue to bring the pH to 1.4. The acidic solution was filtered and the filtrate was extracted twice with ethyl acetate. The extracts were combined and concentrated to give a residue which crystallized upon addition of ethyl acetate to give 1-(2-methanesulfonamidoethyl)tetrazole-5-thiol, mp 131°-132°.

Workup

  1. customthe solid material was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo and 3N hydrochloric acid
  3. additionwas added to the residue
  4. filtrationThe acidic solution was filtered
  5. extractionthe filtrate was extracted twice with ethyl acetate
  6. concentrationconcentrated
  7. customto give a residue which
  8. customcrystallized upon addition of ethyl acetate

Sources & evidence

ORD record
ord-ed6ee3a967bd4b89a6bff7bd3895eb53
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Reaction notes

Loading…