Dimethylformamide → 6-(Chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine

HRID 453280Notes

Reaction equation

HRID 453280 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[S:15][C:16]2[C:21]([N:22]=1)=[CH:20][C:19]([CH2:23]O)=[CH:18][N:17]=2)([O-:7])=[O:6].CN(C=O)C>C(Cl)Cl>[Cl:3][CH2:23][C:19]1[CH:20]=[C:21]2[N:22]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N+:5]([O-:7])=[O:6])[S:15][C:16]2=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 573471802-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanol

Product 1

HCID 585519076-(Chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (3.1 mol, 227 mL) was slowly added to a room temperature suspension of (2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methanol (0.62 mol, 180 g) in CH2Cl2 (1.8 L). DMF (5 mL) was added and the reaction became homogeneous. The reaction was stirred for 1 h, then concentrated under reduced pressure. The crude product was dissolved in CH2Cl2 (150 mL) and concentrated under reduced pressure. The crude product was chased with hexane (200 mL×3)) and dried under vacuum for 16 h to give 6-(chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine as a tan solid (180 g, 94% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe crude product was dissolved in CH2Cl2 (150 mL)
  3. concentrationconcentrated under reduced pressure
  4. customdried under vacuum for 16 h

Sources & evidence

ORD record
ord-a789dff31485448dbeed7fdc2011310e
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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