Ammonium Chloride → HCID 87560084, compound

HRID 1622054Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:16]1[N:21]=[C:20](F)[CH:19]=[CH:18][CH:17]=1)([C:9]1[N:14]=[C:13](F)[CH:12]=[CH:11][CH:10]=1)[CH3:8].[CH:23]1[CH:28]=[CH:27][C:26]([P-:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.[K+].[Cl-].[NH4+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:16]1[N:21]=[C:20]([P:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:26]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)[CH:19]=[CH:18][CH:17]=1)([C:9]1[N:14]=[C:13]([P:29]([C:26]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

Conditions

Temperature: -60 °C

Procedure

14.0 g (48.0 mmol) of 6,6′-(1-(pyridin-2-yl)ethane-1,1-diyl)bis(2-fluoropyridin) were dissolved in 300 ml of tetrahydrofurane and cooled to −60° C. 200 ml (100 mmol) of potassium diphenylphosphide (0.5 M solution in tetrahydrofurane) were added and the mixture was stirred for three days at room temperature. The reaction was hydrolysed with 200 ml of saturated ammonium chloride solution. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed two times with saturated ammonium chloride solution and dried with sodium sulphate. The solvent was removed under reduced pressure to yield 40 g (>100%) of crude product which was used in the next synthesis without further purification.

Workup

extractionThe aqueous layer was extracted three times with ethyl acetate
washThe combined organic layers were washed two times with saturated ammonium chloride solution
dry with materialdried with sodium sulphate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-04ea415d05d3495aa4e4bbe6154a813b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778512B2

Reaction notes

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