Methylamine → 5-[(5-chloro-1H-indol-3-yl)methyl]-2-(methylamino)-1,3-oxazol-4-one

HRID 564850Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[O:16][C:15]([N:17](C)[CH3:18])=[N:14][C:13]1=[O:20].CN>CCOCC>[CH3:18][NH:17][C:15]1[O:16][CH:12]([CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][CH:6]=2)[C:13](=[O:20])[N:14]=1

Participants

Conditions

Temperature: -6 °C

Procedure

To [(5-chloroindol-3-yl)methyl]-2-dimethylamino-2-oxazolin-4-one (200 mg) was added methylamine (20 ml). The mixture was refluxed at −6° C. for 1 hour. Removal of methylamine gave a residue, to which was added ether. The titled compound (120 mg) was obtained as a crystal.

Workup

customRemoval of methylamine
customgave a residue

Sources & evidence

ORD record: ord-d38cdaa381834c4c91c5a1cc3bcf25c6
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169102A

Reaction notes

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