Sodium Hydroxide → HCID 57377802, compound

HRID 1752112Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.[CH2:17]([O:20][NH2:21])[CH:18]=[CH2:19].[OH-].[Na+]>O1CCOCC1.O>[CH2:17]([O:20][NH:21][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1)[CH:18]=[CH2:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (2.00 g, 8.71 mmol), O-allyl-hydroxylamine hydrochloride (1.91 g, 17.42 mmol) and NaOH (0.70 g, 17.42 mmol) in 1,4-dioxane (25 mL) and water (5 mL) was heated at 60° C. for 4 h. The volatiles were removed under reduced pressure. Saturated NaHCO3 solution (100 mL) was added to the residue and the mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield O-allyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-hydroxylamine (XLIII, 2.05 g, 88% yield). ESI-MS (m/z) 267 [M+H]+.

Workup

customThe volatiles were removed under reduced pressure
additionSaturated NaHCO3 solution (100 mL) was added to the residue
extractionthe mixture was extracted with EtOAc (3×25 mL)
washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customthe crude product was purified by flash column chromatography
washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

Sources & evidence

ORD record: ord-941fd463680548e5afe95ee827431e76
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162992B2

Reaction notes

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