Water → HCID 20562623, compound

HRID 1155043Notes

Reaction equation

HRID 1155043 reaction equation
[CH2:1]([C:3]1[NH:12][C:11]2[C:10](=[O:13])[N:8]([CH3:9])[C:7](=[O:14])[N:6]([CH3:15])[C:5]=2[N:4]=1)[CH3:2].[H-].[Na+].[O:18]([CH2:25][CH2:26][CH2:27]Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:1]([C:3]1[N:12]([CH2:27][CH2:26][CH2:25][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]2[C:10](=[O:13])[N:8]([CH3:9])[C:7](=[O:14])[N:6]([CH3:15])[C:5]=2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 68522Benzene, (3-bromopropoxy)-HCID 798388-Ethyltheophylline

Product 1

HCID 20562623HCID 20562623, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 8-ethyltheophylline (20.8 g; 0.1 M) in dry dimethylformamide (100 ml) was added to an oil free suspension of sodium hydride (2.4 g; 0.1 M) in dry dimethylformamide (100 ml) and the mixture was stirred for 30 minutes. 3-Phenoxypropylbromide (21.5 g; 0.1 M) was added and the mixture was stirred at room temperature for 24 hours. The resulting suspension was poured into water and the precipitate was filtered off and dried. The solid was crystallised from ethanol to give 8-ethyl-7-(3-phenoxy propyl)theophylline as white prisms 23.6 g (69%) mp 107°-8°.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. filtrationthe precipitate was filtered off
  3. customdried
  4. customThe solid was crystallised from ethanol

Sources & evidence

ORD record
ord-bc91068b305c448b9927c5b899d121eb
Source dataset
uspto-grants-1981_11
Patent number
US04299832

Reaction notes

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