1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68456183, compound

HRID 2357553Notes

Reaction equation

N12CCCN=C1CCCCC2.[Cl:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([NH:20][CH3:21])=[N:18][OH:19])=[C:15](F)[C:14]=1[I:25]>C1COCC1>[Cl:12][C:13]1[CH:23]=[CH:22][C:16]2[C:17]([NH:20][CH3:21])=[N:18][O:19][C:15]=2[C:14]=1[I:25]

Participants

Conditions

Temperature: 165 °C

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (0.102 g, 0.670 mmol) was added to a solution of 4-chloro-2-fluoro-N′-hydroxy-3-iodo-N-methylbenzamidine (0.200 g, 0.609 mmol) in THF (2 mL) in a sealed microwave tube. The reaction mixture was heated in a microwave at 165° C. for 80 min. The resulting mixture was purified by flash chromatography on silica gel (dichloromethane:hexane 10:90) to give 6-chloro-7-iodo-N-methylbenzo[d]isoxazol-3-amine as an off white solid. MS (ESI, pos.ion) m/z: 308.9 (M+1)

Workup

customThe resulting mixture was purified by flash chromatography on silica gel (dichloromethane:hexane 10:90)

Sources & evidence

ORD record: ord-23eb443beb284c2184317e02b98788ec
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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