Sulfuric Acid → HCID 18988341, compound

HRID 973950Notes

Reaction equation

HRID 973950 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]2[N:21]3[CH:22]=[N:23][CH:24]=[C:20]3[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]2[N:21]3[CH:22]=[N:23][CH:24]=[C:20]3[CH2:19][CH2:18]2)[CH:14]=[CH:15][C:16]=1[N+:6]([O-:9])=[O:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 19987236HCID 19987236, compound

Product 1

HCID 18988341HCID 18988341, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred and cooled (-10° C.) amount of 180 parts of sulfuric acid there were added portionwise 24.0 parts of 5-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole mononitrate (described in U.S. Pat. No. 4,617,307). Stirring at 0° to -10° C. was continued for 2 hours. After cooling to -78° C., the mixture was diluted with 100 parts of water and then neutralized with a solution of 141 parts of NaOH in 200 parts of water, keeping the temperature below 28° C. The whole was basified to pH 9 with an excess of Na2CO3 10% and was filtered when reached room temperature. The precipitate was washed with dichloromethane and the filtrate layers were separated. The aqueous layer was diluted with 100 parts of water and the whole was re-extracted with dichloromethane (4×399 parts). The combined dichloromethane layers were washed with NaCl (sat.), dried, filtered and evaporated, yielding 17.1 parts (75.9%) of 5-(3-chloro-4-nitrophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole (interm. 35).

Workup

  1. stirringStirring at 0° to -10° C.
  2. customthe temperature below 28° C
  3. filtrationwas filtered when
  4. customreached room temperature
  5. washThe precipitate was washed with dichloromethane
  6. customthe filtrate layers were separated
  7. additionThe aqueous layer was diluted with 100 parts of water
  8. extractionthe whole was re-extracted with dichloromethane (4×399 parts)
  9. washThe combined dichloromethane layers were washed with NaCl (sat.)
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-9e06b7294c06457a8710ba1b64b1f607
Source dataset
uspto-grants-1991_11
Patent number
US05066656

Reaction notes

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