Sodium Hydroxide → O-(Diphenylphosphinyl)hydroxylamine
Reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].Cl[P:7](=[O:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.O1CCOCC1>[NH2:2][O:3][P:7](=[O:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Procedure
To hydroxylamine hydrochloride (15.86 g, 228.2 mmol) in water (35 mL) cooled in an ice-salt bath was added 7.1 N aqueous sodium hydroxide (27.4 mL, 194.4 mmol) followed by 1,4-dioxane (100 mL). The solution was vigorously stirred for 15 min and then chlorodiphenylphosphine oxide (20.00 g, 84.52 mmol) was added as a solution in 1,4-dioxane (100 mL). The solution was stirred an additional 15 min as a white precipitate formed. The precipitate was collected and then suspended in cold (0°) 0.25 N aqueous sodium hydroxide (250 mL). The mixture was stirred for 1 h and then the solid was collected, washed with water (100 mL), and thoroughly dried under vacuum to afford the desired intermediate (7.09 g, 36%) as a white solid. 1H-NMR (300 MHz, DMSO-d6) 7.65-7.74 (m, 4H), 7.38-7.42 (m, 6H); 31P-NMR (DMSO-d6) 23.11 (br s, 1P).
Workup
- stirringThe solution was stirred an additional 15 min as a white precipitate
- customformed
- customThe precipitate was collected
- customsuspended in cold (0°) 0.25 N aqueous sodium hydroxide (250 mL)
- stirringThe mixture was stirred for 1 h
- customthe solid was collected
- washwashed with water (100 mL)
- customthoroughly dried under vacuum
Sources & evidence
- ORD record
- ord-d3bba89b599f44f4ba14e098f51a5a05
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338594B2
Reaction notes
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