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

HRID 356516Notes

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 CH2 C12 :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-853d8691c3484b3c9c3c12f2e99bfcc6
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834506

Reaction notes

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