Hydrogen Sulfide → Ethyl thiazole-4-carboxylate

HRID 2187181Notes

Reaction equation

HRID 2187181 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-b60dabf64c924486bc79e217a77e9db1
Source dataset
uspto-grants-2002_06
Patent number
US06407249B1

Reaction notes

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