Ammonium Hydroxide → HCID 18427770, compound

HRID 1279264Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[C:12]1[C:17]([N+:18]([O-])=O)=[C:16]([NH2:21])[CH:15]=[C:14]([CH3:22])[N:13]=1.[NH4+].[OH-].[O-]S(S([O-])=O)=O.[Na+].[Na+]>O.CCOC(C)=O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH:23]([CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH3:29])[C:12]1[C:17]([NH2:18])=[C:16]([NH2:21])[CH:15]=[C:14]([CH3:22])[N:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

N-[2-Bromo-4-(1-methylethyl)phenyl]-6-methyl-3-nitro-N-(1-propyl-butyl)pyridin-2,4-diamine (0.7 g, 1.51 mmol), was suspended between dioxane (30 mL) and water (30 mL) containing conc.NH4OH (1.2 mL). To that Na2S2O4 was added (2.1 g, 12.06 mmol) and the mixture was stirred at 25° C. for 2h. Then an additional 1 g Na2S2O4 was added followd by 10 mL dioxane and 10 mL water. After stirring for 1 h at 25° C. the mixture was patritioned between EtOAc (120 mL) and water (20 mL). The EtOAc was washed with water (100 mL), brine, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel (20% EtOAc/hexanes eluting solvent) to give the product (0.5 g).

Workup

additioncontaining conc
stirringAfter stirring for 1 h at 25° C. the mixture
washThe EtOAc was washed with water (100 mL), brine
dry with materialdried (MgSO4)
customThe residue was chromatographed on silica gel (20% EtOAc/hexanes eluting solvent)

Sources & evidence

ORD record: ord-7fcad03c679f422f96c416a832e823d7
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448261B1

Reaction notes

Loading…