Carbon Dioxide → HCID 178525477, compound

HRID 904869Notes

Reaction equation

HRID 904869 reaction equation
C([Li])CCC.[CH2:6]([N:9]1[C:13]([SH:14])=[N:12][N:11]=[N:10]1)[CH:7]=[CH2:8].[C:15](=[O:17])=[O:16].O>CCCCCC.O1CCCC1>[C:15]([CH2:8][CH:7]=[CH:6][N:9]1[C:13]([SH:14])=[N:12][N:11]=[N:10]1)([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 178418339ButyllithiumHCID 178456705HCID 178456705, compound

Product 1

HCID 178525477HCID 178525477, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

15% solution of n-butyl lithium in hexane (371 ml) was dissolved in dry tetrahydrofuran (150 ml) and cooled to -20° C. To the solution was added dropwise a solution of 1-allyl-1H-tetrazole-5-thiol (38.7 g) in tetrahydrofuran (220 ml) with stirring under a stream of nitrogen gas during a period of 30 minutes. After the addition of solid carbon dioxide, the mixture was stirred for 30 minutes at -10° C. To the mixture was added water (275 ml) and then the resulting mixture was stirred. The aqueous layer was separated adjusted to pH 4.5, washed with ethyl acetate, adjusted to pH 3.8 to 4.0 and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated. The residue was washed with diisopropyl ether to give an oil of 1-(3-carboxy-1-propenyl)-1H-tetrazole-5-thiol (5.5 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes at -10° C
  2. stirringthe resulting mixture was stirred
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-ec2d918ae4284d50913be57b053b1481
Source dataset
uspto-grants-1983_12
Patent number
US04420477

Reaction notes

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