Isoamyl Nitrite → 9-Ethyl-3-carbazolediazonium 1,1,2,3,3,3-hexafluoropropanesulfonate

HRID 1955491

Reaction equation

[F:1][C:2]([F:13])([S:9]([OH:12])(=[O:11])=[O:10])[CH:3]([F:8])[C:4]([F:7])([F:6])[F:5].[CH2:14]([N:16]1[C:28]2[CH:27]=[CH:26][C:25]([NH2:29])=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15].[N:30](OCCC(C)C)=O>O1CCCC1>[F:13][C:2]([F:1])([S:9]([O-:12])(=[O:10])=[O:11])[CH:3]([F:8])[C:4]([F:5])([F:7])[F:6].[CH2:14]([N:16]1[C:28]2[CH:27]=[CH:26][C:25]([N+:29]#[N:30])=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

3 ml of 1,1,2,3,3,3-hexafluoropropanesulfonic acid were added to a solution of 20 ml of tetrahydrofuran (THF) and 4.2 g of 9-ethyl-3-carbazolylamine. After cooling to 0° C., 3 ml of isoamyl nitrite were added dropwise while stirring in such a way that the temperature did not rise above 10° C. After completion of the dropwise addition, the icebath was removed and the stirring of the reaction mixture was continued for a further 4 h. 50 ml of diethyl ether were added, and the precipitate produced was filtered off by suction, washed with a little diethyl ether and dried. 7.4 g of 9-ethyl-3-carbazolediazonium 1,1,2,3,3,3-hexafluoropropanesulfonate was obtained as a yellow, finely crystalline powder.

Workup

customdid not rise above 10° C
additionAfter completion of the dropwise addition
customthe icebath was removed
stirringthe stirring of the reaction mixture
addition50 ml of diethyl ether were added
customthe precipitate produced
filtrationwas filtered off by suction
washwashed with a little diethyl ether
customdried

Sources & evidence

ORD record: ord-ffc836c84ac84afe87e7418fbf9e4dc5
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776652

Linked notes

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