Water → 3-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-2-hydroxypropyl (4-chlorophenoxy)acetate

HRID 1287239Notes

Reaction equation

HRID 1287239 reaction equation
[OH:1][CH:2]([CH2:17][OH:18])[CH2:3][N:4]1[C:13]2[C:12](=[O:14])[N:10]([CH3:11])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[N:6]=[CH:5]1.[Cl:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][C:26](O)=[O:27])=[CH:22][CH:21]=1.O>C1(C)C(C)=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][C:26]([O:18][CH2:17][CH:2]([OH:1])[CH2:3][N:4]2[C:13]3[C:12](=[O:14])[N:10]([CH3:11])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=3[N:6]=[CH:5]2)=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3182DyphyllineHCID 26229(4-Chlorophenoxy)acetic acid

Product 1

HCID 1621393-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-2-hydroxypropyl (4-chlorophenoxy)acetateYield 79%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 7237O-XyleneSolvent

Procedure

27.0 g (0.1 mol) 7-(2,3-dihydroxypropyl)-theophylline and 18.6 g (0.1 mol) p-chlorophenoxyacetic acid were heated in 100 ml xylene for 8 hours in a water separator with the addition of 0.9 g p-toluenesulfonic acid. After cooling down, the xylene was decanted and the residue dissolved in hot isopropanol. After addition of a little water the monoester crystallized out slowly. The yield was 33.4 g (79% yield) of 1-(7-theophyllinyl)-2-hydroxy-3-propyl (p-chlorophenoxyacetate) with a melting point of 81°-83°C.

Workup

  1. temperatureAfter cooling down
  2. customthe xylene was decanted
  3. dissolutionthe residue dissolved in hot isopropanol
  4. additionAfter addition of a little water the monoester
  5. customcrystallized out slowly

Sources & evidence

ORD record
ord-a58d2bbc595d40888a7bab780dadfbba
Source dataset
uspto-grants-1976_10
Patent number
US03984413

Reaction notes

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