Phosgene → HCID 14716204, compound

HRID 846292Notes

Reaction equation

HRID 846292 reaction equation
[CH3:1][O:2][C:3]1[S:4][C:5]([C:9]([OH:11])=O)=[C:6]([CH3:8])[N:7]=1.CN(C)C(=O)C.C(Cl)([Cl:20])=O>O1CCCC1>[CH3:1][O:2][C:3]1[S:4][C:5]([C:9]([Cl:20])=[O:11])=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 31374DimethylacetamideHCID 164948992-Methoxy-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 14716204HCID 14716204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar apparatus to Example 1, 10.4 g (0.06 mole) of 2-methoxy-4-methylthiazole-5carboxylic acid were suspended in 150 ml of tetrahydrofuran, followed by the addition of 0.02 g of N,N-dimethyl-acetamide. Under heating and reflux, phosgene was blown at a rate of 1.1 l/hr for 4.5 hours (0.23 mole). After completion of the blowing, stirring was continued for additional 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 10.8 g of 2-methoxy-4-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 96.2% and 93.9%, respectively.

Workup

  1. temperatureUnder heating
  2. temperaturereflux
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c5ba9920861e45f68e9b6ea65530031d
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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