Thionyl Chloride → HCID 59679997, compound

HRID 1667059Notes

Reaction equation

HRID 1667059 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].S(Cl)([Cl:22])=O>ClCCl.CN(C=O)C>[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 2

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

Product 1

HCID 59679997HCID 59679997, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [6-(2-Nitro-phenyl)-imidazo[2,1-b]thiazol-3-yl]-methanol (1.0 g, 3.63 mmol) in anhydrous dichloromethane (15 ml) was slowly added thionyl chloride (2 ml, 7.5 eq). The solution turned homogenous, followed by development of a yellow precipitate. After 5 minutes, a catalytic amount of DMF (1 drop) was added and the mixture was stirred for 1 hour, concentrated to dryness, chased with CH2Cl2 (2×) then Ether (1×), and dried under reduced pressure. 1.53 g of yellow solid was obtained, and assumed to be quantitative yield. (MS, M++H=294.0)

Workup

  1. concentrationconcentrated to dryness
  2. dry with materialEther (1×), and dried under reduced pressure

Sources & evidence

ORD record
ord-a46c17975ea44bce80bd911a2abbf08f
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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