Hydrochloric Acid → HCID 67792134, compound

HRID 465400Notes

Reaction equation

HRID 465400 reaction equation
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]([NH:20][NH2:21])=[O:19])[NH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N1C=CC=CC=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.Cl>O>[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([N:20]([C:18]([C:15]2[NH:16][CH:17]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=2)=[O:19])[NH2:21])(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 67792022HCID 67792022, compound

Product 1

HCID 67792134HCID 67792134, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 3.29 g (11 mmol) of 4-dodecylpyrrole-2-carboxylic acid hydrazide obtained in Synthesis Example 9 and 35 ml of pyridine, was added little by little 2.23 g (12 mmol) of p-toluenesulfonyl chloride under stirring and cooling with ice. The reaction was carried out for 1.5 hours at room temperature, and the reaction mixture was added to an iced water containing 70 ml of 6N hydrochloric acid. The crystals precipitated by stirring were collected by filtration, washed with water and recrystallized from a mixed solvent of ethanol/water (10/1) to obtain 4.55 g of 4-dodecylpyrrole-2-carboxylic acid p-toluenesulfonylhydrazide as white crystals. The yield was 91% and the melting point was 134.5° to 135.5° C.

Workup

  1. temperaturecooling with ice
  2. customThe crystals precipitated
  3. stirringby stirring
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customrecrystallized from a mixed solvent of ethanol/water (10/1)

Sources & evidence

ORD record
ord-1acae9ecbea2450685994857cca4528d
Source dataset
uspto-grants-1992_10
Patent number
US05153217

Reaction notes

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