Water → HCID 178525591, compound

HRID 1277613Notes

Reaction equation

HRID 1277613 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7](=[S:10])SC)([OH:3])=[O:2].[OH-].[Na+].O.[N-:14]=[N+:15]=[N-:16].[Na+]>CCOCC>[C:1]([CH2:4][CH2:5][N:6]1[C:7]([SH:10])=[N:16][N:15]=[N:14]1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 12458601Methyl 2-carboxyethyldithiocarbamate

Product 1

HCID 178525591HCID 178525591, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 25.37 g. (0.143 mol.) of methyl 2-carboxyethyldithiocarbamate and 5.6 g. (0.143 mol.) of sodium hydroxide in 210 ml. of water was added 9.25 g. (0.143 mol.) of sodium azide. The reaction mixture was refluxed for one hour then cooled, diluted with 100 ml. of ether and acidified to pH 1.7. The layers were separated, the aqueous phase was extracted with ether and the combined extracts were dried (MgSO4) and evaporated to dryness to give a residue which was recrystallized from acetone-chloroform to give 1-(2-carboxyethyl)tetrazole-5-thiol, m.p. 158°-160° C.

Workup

  1. additionTo a mixture of 25.37 g
  2. temperatureThe reaction mixture was refluxed for one hour
  3. temperaturethen cooled
  4. additiondiluted with 100 ml
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ether
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customevaporated to dryness
  9. customto give a residue which
  10. customwas recrystallized from acetone-chloroform

Sources & evidence

ORD record
ord-de53c2df011142c983860242a02c9c7e
Source dataset
uspto-grants-1981_07
Patent number
US04278670

Reaction notes

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