1,1'-Thiocarbonyldiimidazole → HCID 19699368, compound

HRID 863066Notes

Reaction equation

HRID 863066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][CH:7]([NH2:13])[CH2:6][CH2:5]2.[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][CH:7]([N:13]=[C:14]=[S:15])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 196993536,7-Difluoro-1,2,3,4-tetrahydro-2-naphthalenamine

Product 1

HCID 19699368HCID 19699368, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (-)-6,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine (0.56 g, 3.06 mmol), prepared as in Example 8, and 1,1'-thiocarbonyldiimidazole (0.82 g, 4.59 mmol) in 15 mL of ethyl acetate was stirred until the reaction was complete. The solvent was removed by evaporation. Purification of the residue by column chromatography on silica gel (solution: 5% acetone/methylene chloride) gave (-)-6,7-difluoro-2-isothiocyano-1,2,3,4-tetrahydronaphthalene (0.55 g, 2.42 mmol). [α]D25 -15.5° (c=1.0, CH3OH)

Workup

  1. customThe solvent was removed by evaporation
  2. customPurification of the residue by column chromatography on silica gel (solution: 5% acetone/methylene chloride)

Sources & evidence

ORD record
ord-8cff7aea0f1e4074a9fe38122af8fcaa
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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