1,1'-Thiocarbonyldiimidazole → HCID 86590645, compound

HRID 2415286Notes

Reaction equation

[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[C:13]([O:17][C:18](=[O:33])[N:19]([CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH:20]([CH3:22])[CH3:21])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18](=[O:33])[N:19]([CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]=[C:1]=[S:2])=[CH:30][CH:31]=1)([CH3:15])([CH3:16])[CH3:14]

Participants

Conditions

Temperature: -15 °C

Procedure

Thiocarbonyldiimidazole (3.64 g, 20.44 mmol) (Aldrich) was dissolved in N,N-dimethylformamide (3 mL) and the solution was cooled to −15° C. A solution [2-(4-amino-phenoxy)-ethyl]-isopropyl-carbamic acid tert-butyl ester (from step C above) in N,N-dimethylformamide (7 mL) was added dropwise and stirred at room temperature for 90 minutes. The mixture was poured into ice/water (1500 mL) and extracted with ether (4×250 mL). The ether was dried (Na2SO4) and concentrated in vacuo to give 6.5 g, (95%) isopropyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester. Mass spectrum (ES) MH+=367.

Workup

extractionextracted with ether (4×250 mL)
dry with materialThe ether was dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5d3e2b54ad094acf83793404a8e13790
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818663B2

Reaction notes

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