Thionyl Chloride → HCID 12891965, compound

HRID 443890Notes

Reaction equation

HRID 443890 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-e04194c65f774c9ba98088c8235bfbbe
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

Loading…