Ammonium Hydroxide → 6-(4-Nitrophenoxy)benzthiazole-2-ylamine

HRID 1294074Notes

Reaction equation

[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:18]([S-:20])#[N:19].[K+].BrBr.[NH4+].[OH-]>CC(O)=O.O>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]3[N:13]=[C:18]([NH2:19])[S:20][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-nitrophenoxy)aniline (Intermediate 10–1.15 g, 5.0 mmol) in AcOH (5 mL) was added KSCN (729 mg, 7.5 mmol). The mixture was cooled to 0° C. and added a solution of Br2 (256 μL, 5.0 mmol) in AcOH (6 mL) then stirred at room temperature overnight. The mixture was poured into H2O, basified with NH4OH (aq), then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave Intermediate 10A (941.5 mg, 66%): MS m/e 288 (M+1) and Intermediate 10B (223.7 mg, 12%): MS m/e 366, 368 (M+1).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
customthen evaporated
customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record: ord-8fdeaf60ea0847b6ac0a444428f6d631
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238813B2

Reaction notes

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