Nitrogen → Tributyl(methyl)phosphanium bis(trifluoromethanesulfonyl)azanide

HRID 2204014Notes

Reaction equation

N#N.[CH2:3]([P:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH3:6].[N-:16]([S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18].[C:31](=O)(OC)OC>CO>[F:30][C:27]([F:28])([F:29])[S:24]([N-:16][S:17]([C:20]([F:21])([F:22])[F:23])(=[O:18])=[O:19])(=[O:25])=[O:26].[CH3:31][P+:7]([CH2:3][CH2:4][CH2:5][CH3:6])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

In an reactor wherein air was replaced by N2, 300.0 g (1.5 mol) of tributyl phosphine and 1000 mL of methanol were added and cooled to about 0° C. by a ice-bath. 427.6 g (1.5 mol) of trifluoromethanesulfonimide was then added dropwise under strong stirring, and 202.0 g (2.2 mol) of dimethyl carbonate was also added afterwards. After one hour of reaction and mixing, the reaction mixture was transferred to an autoclave, wherein air was removed prior to heating. After 6 hours of reaction at temperature of 180° C. and pressure of from 1.6 MPa to 1.7 MPa, the crude product was obtained after distilling off the unreacted materials and solvent. 705.7 g of methyl tributyl phosphonium bis(trifluoromethanesulfonyl)amide was obtained after washing and drying at 60° C. and 0.1 kPa for 4 hours.

Workup

additionwere added
additionwas also added afterwards
customAfter one hour of reaction
additionmixing
customwas removed
temperatureto heating
customAfter 6 hours of reaction at temperature of 180° C. and pressure of from 1.6 MPa to 1.7 MPa
customthe crude product was obtained
distillationafter distilling off the unreacted materials and solvent

Sources & evidence

ORD record: ord-ea30a88230b5441cb8b7f2c9393ce0c6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365596B2

Reaction notes

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