Dimethylformamide → HCID 59679997, compound

HRID 1170839Notes

Reaction equation

HRID 1170839 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-2d760628a88d4575a48ea47002970e21
Source dataset
uspto-grants-2010_11
Patent number
US07829556B2

Reaction notes

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