Water → HCID 178525591, compound

HRID 895056Notes

Reaction equation

HRID 895056 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 hyroxide 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°.

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-00cb9cac598b407ebdd21d21453d6f6f
Source dataset
uspto-grants-1981_08
Patent number
US04286089

Reaction notes

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