Cis-4-thiocyano-3-buten-2-one → HCID 178467920, compound

HRID 1463791Notes

Reaction equation

HRID 1463791 reaction equation
O.[Na].[SH:3][C:4]1[N:8]([CH3:9])[N:7]=[N:6][N:5]=1.S(/[CH:13]=[CH:14]\[C:15](=[O:17])[CH3:16])C#N>C(O)C>[SH:3][C:4]1[N:8]([CH3:9])[N:7](/[CH:13]=[CH:14]\[C:15](=[O:17])[CH3:16])[NH:6][N:5]=1

Participants

4

Reactant 2

HCID 45085240Cis-4-thiocyano-3-buten-2-one2×HCID 178482031HCID 178482031, compound

Product 1

HCID 178467920HCID 178467920, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 5-mercapto-1-methyltetrazole sodium salt hydrate (1.1 g., 0.008 mole) in aqueous ethanol (15 ml), a solution of cis-4-thiocyano-3-buten-2-one (Compound 28) in ethanol was added dropwise over 5 minutes. A solid suspension was observed forming over the next 2 hours which was stirred at 25° C. for 18 hours. The volatiles were removed in vacuo and the residue was extracted into ethyl acetate and washed thoroughly with water. After drying (MgSO4), the solution was concentrated. The solid residue was purified via column chromatography on silica gel using hexanes/ethyl acetate (3:2) as eluant to yield 1.1 g of a white solid, mp 112°-114° C. IR (nujol) uc=o 1660 cm-1.

Workup

  1. customA solid suspension was observed forming over the next 2 hours which
  2. customThe volatiles were removed in vacuo
  3. extractionthe residue was extracted into ethyl acetate
  4. washwashed thoroughly with water
  5. dry with materialAfter drying (MgSO4)
  6. concentrationthe solution was concentrated
  7. customThe solid residue was purified via column chromatography on silica gel

Sources & evidence

ORD record
ord-ed9be222d7c344df9a075c8e40d5a5bb
Source dataset
uspto-grants-1994_04
Patent number
US05302592

Reaction notes

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