Hydrogen Sulfide → Ethyl thiazole-4-carboxylate

HRID 1268054Notes

Reaction equation

HRID 1268054 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]([N+:10]#[C-:11])=[CH:6]N(C)C)[CH3:2].C(N(CC)CC)C.[SH2:20]>O1CCCC1>[C:4]([C:5]1[N:10]=[CH:11][S:20][CH:6]=1)([O:3][CH2:1][CH3:2])=[O:12]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylate

Product 1

HCID 5003096Ethyl thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-dimethylamino-2-isocyano-acrylic acid ethyl ester (1.0 g) and triethylamine (3.0 g) in tetrahydrofuran (30 mL) is treated with gaseous hydrogen sulfide until all starting material is consumed. The mixture is concentrated to an oil and purified by column chromatography using silica and 25% ethyl acetate-hexanes as the eluant. The purified material (0.61 g) is isolated as an oil.

Workup

  1. customis consumed
  2. concentrationThe mixture is concentrated to an oil
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-e3f745df60e7414fa8cd5dc85737bdd4
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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