1,1'-Thiocarbonyldiimidazole → Ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester

HRID 2415279Notes

Reaction equation

[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[C:13]([O:17][C:18](=[O:32])[N:19]([CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)[CH2:20][CH3:21])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18](=[O:32])[N:19]([CH2:20][CH3:21])[CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]=[C:1]=[S:2])=[CH:29][CH:30]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: -15 °C

Procedure

Thiocarbonyldiimidazole (438 mg, 2.46 mmol) (Aldrich) was dissolved in dimethylformamide (10 mL) and the solution was cooled to −15° C. A solution [2-(4-amino-phenoxy)-ethyl]-ethyl-carbamic acid tert-butyl ester (750 mg, 2.35 mmol) (from step C above) in dimethylformamide (25 mL) was added dropwise, stirred at room temperature for 90 minutes and poured into ice/water. After stirring 30 minutes the precipitate was filtered off, washed with water, and dried under high vacuum to give 453 mg (53%) of ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester. Mass spectrum (ES) MH+=323.

Workup

stirringAfter stirring 30 minutes the precipitate
filtrationwas filtered off
washwashed with water
customdried under high vacuum

Sources & evidence

ORD record: ord-8d25317d4e8c4c03909a46d96bf3825f
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818663B2

Reaction notes

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