Sulfuric Acid → HCID 12892035, compound

HRID 1902631Notes

Reaction equation

HRID 1902631 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[CH2:6][CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10][C:9]=12.S(=O)(=O)(O)O.[OH-].[NH4+]>>[N+:1]([C:15]1[CH:14]=[CH:13][C:12]2[N:8]3[CH2:7][CH2:6][N:5]=[C:9]3[S:10][C:11]=2[CH:16]=1)([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 12891968HCID 12891968, compound

Product 1

HCID 12892035HCID 12892035, compoundYield 80%

Procedure

10 Parts of 2,3-dihydroimidazo[2,1-b]benzothiazole mononitrate are added portionwise to 55.2 parts of concentrated sulfuric acid at 0° C. Upon completion, stirring is continued for 30 minutes at room temperature. The reaction mixture is poured onto crushed ice and the whole is alkalized with ammonium hydroxide at a temperature below 20° C. The product is extracted with a mixture of trichloromethane and methanol (90:10 by volume). The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 160 parts of 1-butanol. The product is filtered off and dried, yielding 8 parts (80%) of 2,3-dihydro-7-nitroimidazol[2,1-b]benzothiazole; mp. 238.9° C.

Workup

  1. additionThe reaction mixture is poured
  2. customonto crushed ice
  3. extractionThe product is extracted with a mixture of trichloromethane and methanol (90:10 by volume)
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 160 parts of 1-butanol
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-93fc154b78d24820b056e80cd015a16b
Source dataset
uspto-grants-1982_12
Patent number
US04364942

Reaction notes

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