Triethylamine → 1-Oxo-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-8-sulfonyl chloride

HRID 2194264Notes

Reaction equation

[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[F:6][C:7]([F:27])([F:26])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C:17]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:16]2=[O:25])=[CH:11][CH:10]=1.CCN(CC)CC>C(Cl)(Cl)Cl>[O:25]=[C:16]1[C:17]2([CH2:24][CH2:23][N:22]([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:21][CH2:20]2)[CH2:18][CH2:19][N:15]1[C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]([F:27])([F:6])[F:26])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 405 mg (2.91 mmol) sulfuryl chloride in 15 mL anhydrous CHCl3 at 0° C. was slowly added a mixture of 915 mg (2.91 mmol) 2-(4-(trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one and 295 mg (2.91 mmol) NEt3 over a period of 30 min and stirred at 0° C. for 1 h. the mixture was allowed to warm to room temperature stirred for 1 h and 405 mg (2.91 mmol) sulfuryl chloride was added. The mixture was stirred for 5 h at room temperature, evaporated to dryness and used without further purification in the consecutive step. MS (ESI): 315.2 (M-SO2Cl)H+.

Workup

temperatureto warm to room temperature
stirringstirred for 1 h
stirringThe mixture was stirred for 5 h at room temperature
customevaporated to dryness
customused without further purification in the consecutive step

Sources & evidence

ORD record: ord-17a07f2ba16e4f36953d7049bb5a9e16
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329904B2

Reaction notes

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