4-Aminoantipyrine → HCID 22797767, compound

HRID 2398723Notes

Reaction equation

HRID 2398723 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:24]=[C:25]=[S:26])(=[O:3])[CH3:2].[CH3:27][C:28]1[N:33]([CH3:34])[N:32]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30](=[O:31])[C:29]=1[NH2:41]>C1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH:24][C:25]([NH:41][C:29]1[C:30](=[O:31])[N:32]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:33]([CH3:34])[C:28]=1[CH3:27])=[S:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 21514-AminoantipyrineHCID 12899825HCID 12899825, compound

Product 1

HCID 22797767HCID 22797767, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 5 ml of anhydrous benzene were added 390 mg (1 mmol) of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl isothiocyanate and 200 mg (1 mmol) of 4-aminoantipyrine and the mixture was heated at 60°-70° C. for 4 hours and allowed to cool to room temperature. Crystals formed were filtered off and recrystallized from petroleum ether to give pure crystals melting between 148° and 150° C. (uncorrected). Yield: 300 mg (61%).

Workup

  1. temperaturethe mixture was heated at 60°-70° C. for 4 hours
  2. customCrystals formed
  3. filtrationwere filtered off
  4. customrecrystallized from petroleum ether
  5. customto give pure crystals
  6. custommelting between 148° and 150° C.

Sources & evidence

ORD record
ord-42474967a84e4ba38bd7f45f006bd151
Source dataset
uspto-grants-1977_05
Patent number
US04025622

Reaction notes

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