1,1'-Thiocarbonyldiimidazole → HCID 86590646, compound

HRID 2415263Notes

Reaction equation

HRID 2415263 reaction equation
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[S:7])C=1.[C:13]([O:17][C:18](=[O:31])[NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=CC(N)=[CH:26][CH:25]=1)([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18](=[O:31])[NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:10][C:9]([N:8]=[C:6]=[S:7])=[CH:26][CH:25]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11780454HCID 11780454, compound

Product 1

HCID 86590646HCID 86590646, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a cooled (−15° C.) solution of 1,1-thiocarbonyidiimidazole (756 mg, 4.115 mmol) (Aldrich) in N,N-dimethylformamide (11 mL) was added dropwise a solution of [3-(4-aminophenoxy)propyl]carbamic acid tert-butyl ester (1.02 g, 3.84 mmol) (from Step B above) in N,N-dimethylformamide (11 mL) over 25 minute. After the addition was complete, the mixture was stirred at −15° C. for 20 minute and then at room temperature for 1 h. Ice-water was added and the mixture was extracted with ether. The ether layer was dried (MgSO4), filtered, and evaporated. The residue was purified on silica gel with 85:15 hexane/ethyl acetate to give [3-(4-isothiocyanatophenoxy)propyl]-carbamic acid tert-butyl ester (1.07 g, 91% yield). HRMS, observed: 308.1197; Calcd for M+:308.1195.

Workup

  1. additionAfter the addition
  2. waitat room temperature for 1 h
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe ether layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel with 85:15 hexane/ethyl acetate

Sources & evidence

ORD record
ord-6afbc6a0bc0749cc81ba42a98d3b7ac2
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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