1,2-Dichloroethane → 5-Nitrothiophene-2-carboxamide

HRID 385740Notes

Reaction equation

HRID 385740 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH4+].[Cl-].C1C=CC2N(O)N=[N:20]C=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[N+:1]([C:4]1[S:8][C:7]([C:9]([NH2:20])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 805915-Nitro-2-thenoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 3147105-Nitrothiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Nitro-2-thiophenecarboxylic acid (7.50 g, 43.3 mmol), NH4Cl (6.95 g, 130 mmol), HOBT (8.62 g, 56.3 mmol), and EDC (12.46 g, 65.0 mmol) were combined with DMF (100 mL) and DIEA (15.13 mL, 87.0 mmol). The reaction was stirred at room temperature overnight. The brown solution was concentrated, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. The solid residue was triturated with CH2Cl2 and filtered to isolate the title compound as a colorless solid.

Workup

  1. concentrationThe brown solution was concentrated
  2. additiondiluted with saturated NaHCO3
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was triturated with CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6a2e4d6237f6404db21ffed4eb9386da
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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