Phosphorus oxychloride → 2-Chloro-4-(3-nitrothiophen-2-yl)thiazole

HRID 1519908Notes

Reaction equation

HRID 1519908 reaction equation
CO[C:3]1[S:4][CH:5]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])[N:7]=1.C(=O)(O)[O-].[Na+].O=P(Cl)(Cl)[Cl:23]>O>[Cl:23][C:3]1[S:4][CH:5]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])[N:7]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 687557612-Methoxy-4-(3-nitrothiophen-2-yl)thiazole

Product 1

HCID 687551102-Chloro-4-(3-nitrothiophen-2-yl)thiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-methoxy-4-(3-nitrothiophen-2-yl)thiazole (403 mg, 1.66 mmol) in POCl3 (2 mL) was heated at 60° C. for 1 h then to 100° C. for a further 2 h. The resulting solution was cooled to room temperature and diluted with cold H2O then saturated aqueous sodium bicarbonate. The mixture was extracted with methylene chloride and the combined organic phases were dried (Na2SO4), filtered and concentrated under vacuum to give 2-chloro-4-(3-nitrothiophen-2-yl)thiazole. Retention time (min)=2.550, method [1], MS(ESI) 246.9 (M+H).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. dry with materialthe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b1cd4844a12549c9822060de6fdbfb56
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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