Dimethylformamide → HCID 57448415, compound

HRID 547339Notes

Reaction equation

HRID 547339 reaction equation
CN(C)C=O.[C:6]([Cl:11])(=O)C(Cl)=O.[NH:12]1[C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[S:14]C1=S.C([O-])(O)=O.[Na+]>ClCCCl.O>[Cl:11][C:6]1[S:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[N:12]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 14062658HCID 14062658, compound

Product 1

HCID 57448415HCID 57448415, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

To an ice-cold mixture of dimethylformamide (DMF, 1.1 mL) and DCE (8 mL) was added dropwise a solution of oxalyl chloride (1.73 mL) in DCE (4 mL). A white precipitate formed, and the reaction mixture was stirred at rt for 5 min. [1,3]Thiazolo[5,4-c]pyridine-2(1H)-thione (1 g, 6 mmol) was added in portions, and the reaction mixture was stirred at reflux for 3 h. After cooling to rt, the reaction mixture was treated with water (20 mL) and saturated (satd.) aqueous (aq.) NaHCO3 (100 mL) and then extracted with ethyl acetate (EtOAc) (2×100 mL). The combined organic layers were dried, filtered and concentrated to provide the desired product as a brown solid (1 g, 87%). 1H NMR (400 MHz, CDCl3): 9.11 (d, J=0.8, 1H), 8.68 (d, J=5.6, 1H), 7.85 (dd, J=5.6, 0.8, 1H). MS (ESI): mass calcd. for C6H3ClN2S, 169.97; m/z found, 171.0 [M+H]+.

Workup

  1. customA white precipitate formed
  2. additionwas added in portions
  3. temperatureat reflux for 3 h
  4. extractionextracted with ethyl acetate (EtOAc) (2×100 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b6897a8c3a344b2fb15b068a6b7ce098
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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