1,1'-Thiocarbonyldiimidazole → HCID 86590647, compound

HRID 2415266Notes

Reaction equation

C1N=CN([C:6](N2C=NC=C2)=[S:7])C=1.[C:13]([O:17][C:18](=[O:33])[N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH2:20][CH3:21])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18](=[O:33])[N:19]([CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]=[C:6]=[S:7])=[CH:30][CH:31]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: -20 °C

Procedure

To a cooled (−20° C.) solution of 1,1-thiocarbonyldiimidazole (811 mg, 4.415 mmol) (Aldrich) in N,N-dimethylformamide (11 mL) was added dropwise a solution of [3-(4-aminophenoxy)propyl]-ethyl-carbamic acid tert-butyl ester (1.175 g, 3.99 mmol) (from Step B above) in N,N-dimethyl-formamide (11 mL) over 25 minute. After the addition was complete, the mixture was stirred at −20° C. for 20 minutes and then at room temperature for 1 hour. Ice-water was added and the mixture was extracted with ether. The ether layer was dried (Na2SO4), filtered, and evaporated. The residue was purified on silica gel with 85:15 hexane/ethyl acetate to give ethyl-[3-(4-isothiocyanatophenoxy)propyl]carbamic acid tert-butyl ester (1.24 g, 92% yield). HRMS, Observed: 336.1496; Calcd for M+:336.1508.

Workup

additionAfter the addition
waitat room temperature for 1 hour
extractionthe mixture was extracted with ether
dry with materialThe ether layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customThe residue was purified on silica gel with 85:15 hexane/ethyl acetate

Sources & evidence

ORD record: ord-3cce161ef1cb4d75925668befcd825b1
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818663B2

Reaction notes

Loading…