Dimethylformamide → HCID 59679997, compound

HRID 888243Notes

Reaction equation

HRID 888243 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[N:16]([CH:17]=1)[C:15]([CH2:18]O)=[CH:14][S:13]2)([O-:3])=[O:2].O=S(Cl)[Cl:22].CN(C=O)C>ClCCl>[Cl:22][CH2:18][C:15]1[N:16]2[CH:17]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[N:11]=[C:12]2[S:13][CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 25232523[6-(2-Nitrophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]methanol

Product 1

HCID 59679997HCID 59679997, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of [6-(2-nitro-phenyl)-imidazo[2,1-b]thiazol-3-yl]-methanol (165 g, 0.6 mol) in dichloromethane (1.65 L) was added SOCl2 (400 mL, 5.5 mol) at room temperature. DMF (0.3 mL) was added and the reaction mixture was stirred at 30° C. (2 h). The reaction mixture was cooled to 0° C., and the precipitate was collected by filtration and dried in vacuo to give 3-chloromethyl-6-(2-nitro-phenyl)-imidazo[2,1-b]thiazole as a white solid (174 g, 99% yield).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-40b41923f60241a2b5c72495144a0fa7
Source dataset
uspto-grants-2012_08
Patent number
US08247565B2

Reaction notes

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