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

HRID 978006Notes

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 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 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
filtrationAfter filtering
customthe solid was dried in vacuo at 45° C. for 12 hours
customThe title compound was purified by chromatography
customrecrystallized from hexane, m.p. about 104°-106.5° C.

Sources & evidence

ORD record: ord-ed882c1c151e493ca171f845bd3db601
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663333

Reaction notes

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