Sodium Hydroxide → 1-(Cyclohexylmethyl)-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

HRID 276294

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[S:16][CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:13]1.Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+]>CN(C=O)C>[CH:23]1([CH2:22][N:13]2[C:14]3([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15][S:16][C:12]2=[N:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (Method C2a; 0.10g, 0.3432 mmol) and bromomethylcyclohexane (1.00 mL) in DMF (1.00 mL) was added NaOH (approx. 0.13 g). The resulting mixture was stirred at 45° C. for 2 d during which it turned from deep red to bright orange. The reaction mixture was then cooled to room temp., filtered and concentrated under reduced pressure. The residual oil was purified by chromatography (SiO2; 5% EtOAc/hex) to afford 1-(cyclohexylmethyl)-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (0.042 g, 32%) mp 85-7° C.

Workup

temperatureThe reaction mixture was then cooled to room temp.
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residual oil was purified by chromatography (SiO2; 5% EtOAc/hex)

Sources & evidence

ORD record: ord-9be90650ac23408a99f66696544e0098
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

Loading…