Guanidine Hydrochloride → HCID 178473939, compound

HRID 2215645Notes

Reaction equation

HRID 2215645 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15](O)=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].S(Cl)(Cl)=O.Cl.[NH2:23][C:24]([NH2:26])=[NH:25].[OH-:27].[Na+]>>[NH:25]([CH2:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([C:14](=[O:27])[CH3:15])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[C:24]([NH2:26])=[NH:23]

Participants

5

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 69550Acefylline

Product 1

HCID 178473939HCID 178473939, compound

Conditions

Temperature
45 °C

Procedure

Theophylline-7-acetic acid (TAA) (0.42 moles, 100 grams) is admixed with excess thionyl chloride (SOC12) and slowly heated to 45° C. and refluxed for 2 hours. When reaction is completed, the excess SOC12 is removed under vacuum evaporation at 50° C., in the presence of benzene (80 grams). The vacuum evaporation with benzene is repeated three times to eliminate all residual SOC12. The resultant compound, theophylline-7-acetyl chloride (“TAC”) is added to a solution of guanidine hydrochloride (0.25 mols, 60 grams) and 5 equivalents of 2 normal sodium hydroxide at 0° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customWhen reaction
  3. customthe excess SOC12 is removed under vacuum evaporation at 50° C., in the presence of benzene (80 grams)
  4. customThe vacuum evaporation with benzene

Sources & evidence

ORD record
ord-226a71ac798e41ce9f7cdedbc0bb4c70
Source dataset
uspto-grants-2006_09
Patent number
US07109329B2

Reaction notes

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