Potassium Hydroxide → HCID 13525043, compound

HRID 1981585Notes

Reaction equation

HRID 1981585 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=3[NH2:24])=[N:9][C:8]=2[N:7]([CH2:25]CC)[C:5]1=[O:6])CC.[OH-].[K+].[NH4+]=S>>[NH2:24][C:16]1[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:15]=1[C:10]1[NH:11][C:12]2[C:13](=[O:14])[N:4]([CH3:1])[C:5](=[O:6])[N:7]([CH3:25])[C:8]=2[N:9]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 21293470HCID 21293470, compound

Product 1

HCID 13525043HCID 13525043, compound

Procedure

1,3-dipropyl-8-(2-amino-4-nitrophenyl)xanthine (0.007 mol) was dissolved in 20 ml boiling 2.5N KOH. Five ml of 22% ammonium sulfide was added, and the solution was removed from heat after 1 minute. HCl was added to pH 8 in a hood, and the product was collected by filtration and washed with water. About 25% of the product was a sulfur-containing impurity. Since this impurity appeared to protect the xanthine from oxidation, no attempt was made to further purify the xanthine. 8-(2,4-diaminophenyl)theophylline was synthesized in the same way.

Workup

  1. customthe solution was removed
  2. temperaturefrom heat after 1 minute
  3. additionHCl was added to pH 8 in a hood
  4. filtrationthe product was collected by filtration
  5. washwashed with water
  6. additioncontaining impurity
  7. customto further purify the xanthine

Sources & evidence

ORD record
ord-10fcdd17f0d3488ebcf8c8eea289c890
Source dataset
uspto-grants-1986_06
Patent number
US04593095

Reaction notes

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