2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 14795475, compound

HRID 1939229Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[NH2:13][C:14]1[C:15](=[O:28])[N:16]([CH2:25][CH2:26][CH3:27])[C:17](=[O:24])[N:18]([CH2:21][CH2:22][CH3:23])[C:19]=1[NH2:20].CCOC(/N=N/C(OCC)=O)=O>C(O)C.C(O)(=O)C>[CH2:25]([N:16]1[C:15](=[O:28])[C:14]2[NH:13][C:11]([C:9]3[CH:8]=[CH:7][C:6]4[O:1][CH2:2][CH2:3][O:4][C:5]=4[CH:10]=3)=[N:20][C:19]=2[N:18]([CH2:21][CH2:22][CH3:23])[C:17]1=[O:24])[CH2:26][CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

2.18 g (0.013 mol) of 1,4-benzodioxan-6-aldehyde, 80 ml of ethanol and 2.4 ml of glacial acetic acid are mixed together and 2.8 g (0.012 mol) of 5,6-diamino-1,3-dipropyluracil are added thereto. The clear solution is refluxed for 21/4 hours and then cooled to 60° C. At this temperature, 2.1 ml (0.013 mol) of diethylazodicarboxylate are added dropwise and the viscous suspension produced is mixed with 80 ml of ethanol and refluxed for 2 hours. After a further 20 hours at ambient temperature the mixture is cooled to 5° C., the solid matter is filtered under suction and washed with ethanol and ether. 4.1 g of the title compound are obtained in the form of a grey solid (=92% of theory), melting point 280°-282° C.

Workup

temperatureThe clear solution is refluxed for 21/4 hours
customthe viscous suspension produced
temperaturerefluxed for 2 hours
temperatureAfter a further 20 hours at ambient temperature the mixture is cooled to 5° C.
filtrationthe solid matter is filtered under suction
washwashed with ethanol and ether

Sources & evidence

ORD record: ord-26aafcd453ec4ad18db9096ede3b9889
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696124

Reaction notes

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