Ammonium thiocyanate → 2'-Hydroxy[1,1':3',1"-terphenyl]5'-yl thiocyanate

HRID 1085411Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:20][C:21]#[N:22].[NH4+]>CO>[OH:19][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][C:11]([S:20][C:21]#[N:22])=[CH:10][C:9]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: -5 °C

Procedure

2,6,-Diphenylphenol (100.0 g, 0.406 mole) and ammonium thiocyanate (67.99 g, 0.893 mole) were suspended in methanol (150 ml) in a three necked round bottom flask equipped with magnetic stirrer, thermometer and bubbler. The reaction mixture was cooled to -5° C. in an acetone/ice bath and chlorine gas bubbled through the solution for three hours. Maintaining the temperature below 10° C., ammonia gas was bubbled through the reaction for 2 hours. The contents of the flask were then poured into iced distilled water (250 ml) and allowed to stand for 12 hours in the refrigerator. After filtering, the solid was dried in vacuo at 45° C. for 12 hours. The title compound was purified by chromatography on silica and recrystallized from hexane, m.p. about 104°-106.5° C.

Workup

customequipped with magnetic stirrer
customchlorine gas bubbled through the solution for three hours
temperatureMaintaining the temperature below 10° C., ammonia gas
customwas bubbled through the reaction for 2 hours
additionThe contents of the flask were then poured
distillationinto iced distilled water (250 ml)
filtrationAfter filtering
customthe solid was dried in vacuo at 45° C. for 12 hours
customThe title compound was purified by chromatography on silica
customrecrystallized from hexane, m.p. about 104°-106.5° C.

Sources & evidence

ORD record: ord-4346db93a89a40678cd834cfb49d5616
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05010080

Reaction notes

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