Potassium thiocyanate → 1-(4,6-Difluoroindan-1-yl)-1,3-dihydroimidazole-2-thione

HRID 863069Notes

Reaction equation

HRID 863069 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH:12][CH2:13][CH:14](OC)OC.[S-:19][C:20]#[N:21].[K+]>Cl.C(O)C.O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[N:12]1[CH:13]=[CH:14][NH:21][C:20]1=[S:19]

Participants

6

Reactant 2

HCID 516872Potassium thiocyanateHCID 19699493(4,6-Difluoroindan-1-yl)-(2,2-dimethoxyethyl)amine

Product 1

HCID 196992771-(4,6-Difluoroindan-1-yl)-1,3-dihydroimidazole-2-thioneYield 48.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of (4,6-difluoroindan-1-yl)-(2,2-dimethoxyethyl)amine (11.68 g, 45.9 mmol), potassium thiocyanate (4.46 g, 45.9 mmol) in 21.6 mL of 12N hydrochloric acid, 86 mL of ethanol and 86 mL of water was heated at 80° to 85° C. for 15 hours. The mixture was cooled in an ice bath and diluted with water giving a crystalline material. The material was isolated by filtration and the filter residue was rinsed with cold ethanol (2×25 mL) and 50 mL of diethyl ether. Drying gave 1-(4,6-difluoroindan-1-yl)-1,3-dihydroimidazole-2-thione (5.65 g, 22.2 mmol), m.p. 205°-207° C.

Workup

  1. temperaturewas heated at 80° to 85° C. for 15 hours
  2. temperatureThe mixture was cooled in an ice bath
  3. customThe material was isolated by filtration
  4. washthe filter residue was rinsed with cold ethanol (2×25 mL) and 50 mL of diethyl ether
  5. customDrying

Sources & evidence

ORD record
ord-469010e7433e499a8cf7b1a9783f48f8
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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