Bromine → 5-tert-Butyl-2-methyl-4-thiocyanato-phenylamine

HRID 1003872Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[C:9]([NH2:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[S:13](C#N)[C:14]#[N:15].[Na].BrBr.[Br-].[Na+]>C(=O)(O)[O-].[Na+].CO>[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([NH2:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.0 g (6.1 mmol) of 5-tert-butyl-2-methyl-phenylamine prepared in Example CCCC, sodium thiocyanide (1.62 g, 20.0 mmol) and MeOH (4.0 mL) was cooled to 0° C. and treated via addition funnel with a solution of bromine (0.35 mL, 6.7 mmol), sodium bromide (0.63 g, 6.13 mmol), and MeOH (5.0 mL). The mixture was stirred for 30 minutes and then carefully diluted with saturated sodium bicarbonate. The mixture was extracted with CH2Cl2 and the organic layers combined, dried (Na2SO4), and the solvent evaporated. The residue was then submitted to column chromatography (4:1 CH2Cl2 :hexanes to 19:1 CH2Cl2 :hexanes +1% MeOH) to provide the title compound. 1H NMR (CDCl3) δ 1.42 (s, 9 H), 2.09 (s, 3 H), 3.80 (bs, 2 H), 6.69 (s, 1 H), 7.35 (s, 1 H).

Workup

extractionThe mixture was extracted with CH2Cl2
dry with materialdried (Na2SO4)
customthe solvent evaporated

Sources & evidence

ORD record: ord-723202709cf8450792359f5e78024308
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046355

Reaction notes

Loading…