Oxalyl chloride → 5-Nitrothiophene-3-carbonyl chloride

HRID 889622Notes

Reaction equation

HRID 889622 reaction equation
[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:15])=O>ClCCl>[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]([Cl:15])=[O:11])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 27772675-nitrothiophene-3-carboxylic acid

Product 1

HCID 132755585-Nitrothiophene-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-nitro-thiophene-3-carboxylic acid (5.0 g, 29 mmol) in dichloromethane (60 ml) was added oxalyl chloride (2.93 ml, 35 mmol) at room temperature. The mixture was stirred for 30 minutes at room temperature then for 30 minutes at 50° C. The solvent was evaporated and the residue suspended in tetrahydrofuran (30 ml). The solution was used without purification in the next step.

Workup

  1. waitfor 30 minutes at 50° C
  2. customThe solvent was evaporated
  3. customThe solution was used without purification in the next step

Sources & evidence

ORD record
ord-195c8100da24441c91ddbea8e4b4529a
Source dataset
uspto-grants-2012_08
Patent number
US08252936B2

Reaction notes

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