Hydrogen Sulfide → Ethyl thiazole-4-carboxylate

HRID 1249896Notes

Reaction equation

HRID 1249896 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-992998d4ecc344069a2d4cd2595917c0
Source dataset
uspto-grants-2002_01
Patent number
US06335350B1

Reaction notes

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