Thionyl Chloride → HCID 12891965, compound

HRID 1759396Notes

Reaction equation

HRID 1759396 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH:12][CH2:13][CH2:14]O)=[N:9][C:8]=2[CH:16]=1)([O-:3])=[O:2].S(Cl)([Cl:19])=O>CN(C)C=O>[ClH:19].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]3=[N:12][CH2:13][CH2:14][N:9]3[C:8]=2[CH:16]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 30187692-[(5-Nitro-1,3-benzothiazol-2(3H)-ylidene)amino]ethan-1-ol

Product 1

HCID 12891965HCID 12891965, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 19 parts of 2-[(5-nitro-2-benzothiazolyl)amino]ethanol in 18 parts of N,N-dimethylformamide is added dropwise (slowly) a solution of 10.7 parts of thionyl chloride in 207 parts of N,N-dimethylformamide. Upon completion, the mixture is stirred and heated slowly to reflux and stirring at reflux is continued for 4 hours. After cooling, the precipitated product is filtered off and washed with N,N-dimethylformamide and 2,2'-oxybispropane, yielding 17.5 parts (85%) of 2,3-dihydro-6-nitroimidazo[2,1-b]benzothiazole monohydrochloride; mp. 314°-316° C. (dec.).

Workup

  1. stirringUpon completion, the mixture is stirred
  2. temperatureheated slowly
  3. temperatureto reflux
  4. stirringstirring
  5. temperatureat reflux
  6. temperatureAfter cooling
  7. filtrationthe precipitated product is filtered off
  8. washwashed with N,N-dimethylformamide and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-b532ab1050dd43bfa923848129873376
Source dataset
uspto-grants-1982_07
Patent number
US04340738

Reaction notes

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