Phenyl Isothiocyanate → HCID 66820810, compound

HRID 386388Notes

Reaction equation

[CH3:1][Si:2]([CH:5]=[N+:6]=[N-:7])([CH3:4])[CH3:3].CC[CH2:10][CH2:11][CH2:12][CH3:13].[Li]CCCC.[N:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:20]=[S:21].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCCC1.O>[C:22]1([N:19]2[C:20]([S:21][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:5]([Si:2]([CH3:4])([CH3:3])[CH3:1])[N:6]=[N:7]2)[C:27]2[C:26](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (trimethylsilyl)diazomethane in hexane (2M, 1.74 mL, 3.5 mmol) in tetrahydrofuran (10 mL) at −78° C. was added dropwise n-BuLi and the mixture was stirred at −78° C. for 1 hour. Isothiocyanatobenzene (500 mg, 2.9 mmol) in THF (4 mL) was added and the mixture was stirred at −78° C. for 1 hour. Ethyl bromoacetate (484 mg, 2.9 mmol) was then added and the mixture was stirred at −78° C. for 30 min. and then at 0° C. for additional 30 min. Iced water was added to the reaction and the mixture was extracted with ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give ethyl 2-(1-(naphthalen-1-yl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-ylthio)acetate as a yellow oil, that was used in the next step without further purification (1 g, 89%).

Workup

stirringthe mixture was stirred at −78° C. for 1 hour
stirringthe mixture was stirred at −78° C. for 30 min.
waitat 0° C. for additional 30 min
additionwas added to the reaction
extractionthe mixture was extracted with ether
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cb87217628124228984e2c4181c8e1e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372807B2

Reaction notes

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