1,1'-Thiocarbonyldiimidazole → HCID 86619831, compound

HRID 1426875Notes

Reaction equation

HRID 1426875 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[S:2].[C:13]([O:17][C:18]1C=C([CH:22]=[C:23]([F:25])[CH:24]=1)N)([CH3:16])([CH3:15])[CH3:14]>ClCCl.O>[C:13]([O:17][C:18]1[CH:11]=[C:12]([N:8]=[C:1]=[S:2])[CH:22]=[C:23]([F:25])[CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 667439143-tert-Butoxy-5-fluoroaniline

Product 1

HCID 86619831HCID 86619831, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

1,1′-Thiocarbonyldiimidazole (423 g, 2.37 mol) was dissolved in dichloromethane (3200 ml). The mixture was stirred under N2 atmosphere while a solution of 3-tert-butoxy-5-fluoroaniline (435 g, 2.37 mol) in dichloromethane (800 ml) was added slowly within 2 h. Then the mixture was kept stirring at 20° C. for 16 h. The mixture was diluted with water (3000 ml). The separated dichloromethane phase was washed again with water (3000 ml) before dried with anhydrous Na2SO4 for 2 h. The mixture was filtered and the filtrate was concentrated under vacuum to remove solvent to give 1-tert-butoxy-3-fluoro-5-isothiocyanato-benzene (499 g). 1H-NMR (400 MHz, CDCl3): 6.63-6.68 (m, 3H), 1.37 (s, 9H).

Workup

  1. additionwas added slowly within 2 h
  2. washThe separated dichloromethane phase was washed again with water (3000 ml)
  3. dry with materialbefore dried with anhydrous Na2SO4 for 2 h
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customto remove solvent

Sources & evidence

ORD record
ord-738885d9a50a4387a89b03d533c25bf4
Source dataset
uspto-grants-2015_01
Patent number
US08933108B2

Reaction notes

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