1,1'-Thiocarbonyldiimidazole → 5-Isothiocyanato-indan-2-ol

HRID 1422849Notes

Reaction equation

HRID 1422849 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([OH:11])[CH2:5]2.C1N=CN([C:17](N2C=NC=C2)=[S:18])C=1>C(Cl)Cl>[N:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([OH:11])[CH2:5]2)=[C:17]=[S:18]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 215550315-amino-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 866197015-Isothiocyanato-indan-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-indan-2-ol (149 mg, 1 mmol) was dissolved in CH2Cl2 (10 mL) and TCDI (thiocarbodiimidazole, 178 mg, 1 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 30 min. Silica gel was added to the reaction mixture and dried. Purification of silica gel coated crude product by column chromatography (EtOAc:Hexane=3:7) afforded the title product as a white solid (132 mg).

Workup

  1. additionSilica gel was added to the reaction mixture
  2. customdried
  3. customPurification of silica gel coated crude product by column chromatography (EtOAc:Hexane=3:7)

Sources & evidence

ORD record
ord-b264c3878bbd4c318c715a244ce26e27
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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