Iodonium, diphenyl-, hexafluorophosphate(1-) (1:1) → HCID 86600086, compound

HRID 2373146Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[F:25][P-:26]([F:31])([F:30])([F:29])([F:28])[F:27].[C:32]1([I+]C2C=CC=CC=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C([O-])(=O)C1C=CC=CC=1.[Cu+].CCOCC>[F:25][P-:26]([F:31])([F:30])([F:29])([F:28])[F:27].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S+:18]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 10-(4-butylphenyl)-10H-phenothiazine (83) (1.44 g, 4.34 mmol), diphenyliodonium hexafluorophosphate (1.85 g, 4.34 mmol) and copper (I) benzoate (0.10 g) was heated at 120° C. for 3 hours under nitrogen. Upon cooling to ambient temperature, the mixture was transferred to a mortar-and-pestle and 50 ml of ether was added. The solid was finely powdered, washed with ether, collected by filtration and washed three times with ether. Without further purification, it was isolated in 98.2% (2.36 g) yield as a pale yellow solid.

Workup

temperatureUpon cooling to ambient temperature
additionwas added
washwashed with ether
filtrationcollected by filtration
washwashed three times with ether
customWithout further purification
customit was isolated in 98.2% (2.36 g)
customyield as a pale yellow solid

Sources & evidence

ORD record: ord-4160a45f63744d99a0b8e64e53335438
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459106B2

Reaction notes

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