Ammonium thiocyanate → HCID 59627520, compound

HRID 1623566Notes

Reaction equation

HRID 1623566 reaction equation
[NH4+].[N:2]#[C:3][S-:4].[CH2:5]([O:7][C:8](=[O:14])[CH2:9][CH2:10][C:11](Cl)=[O:12])[CH3:6].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[F:23])[NH2:19]>CC#N>[CH2:5]([O:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([NH:2][C:3]([NH:19][C:18]1[CH:20]=[CH:21][C:22]([F:23])=[C:16]([F:15])[CH:17]=1)=[S:4])=[O:12])[CH3:6]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 774693,4-DifluoroanilineHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl ester

Product 1

HCID 59627520HCID 59627520, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of thiocyanic acid, ammonium salt (5 g, 0.065 mol) in CH3CN (42 ml) was stirred for 15 min. at r.t. 4-Chloro-4-oxo-butanoic acid ethyl ester (0.061 mol) was added dropwise and the mixture was stirred for 30 min. at 60° C. The mixture was cooled to 0° C. and then 3,4-difluoroaniline (6 mL, 0.061 mol) was added dropwise. The reaction mixture was stirred for 30 min. at r.t. The mixture was then quenched with ice-water and stirred for 15 min. at 0° C. The mixture was filtered through a sinter funnel, dried and azeotroped with toluene to remove remaining water. Yield: 16.40 g of intermediate D5 (85%, yellow solid).

Workup

  1. stirringthe mixture was stirred for 30 min. at 60° C
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringThe reaction mixture was stirred for 30 min. at r.t
  4. customThe mixture was then quenched with ice-water
  5. stirringstirred for 15 min. at 0° C
  6. filtrationThe mixture was filtered through a sinter funnel
  7. customdried
  8. customazeotroped with toluene
  9. customto remove

Sources & evidence

ORD record
ord-e048c38fe9d14ca38654ffe2ae7883fe
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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