1,1'-Thiocarbonyldiimidazole → HCID 59707357, compound

HRID 1881365Notes

Reaction equation

HRID 1881365 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])=[CH:8][C:7]=2[C:6]([NH2:13])=[CH:5][CH:4]=1.C1N=CN([C:19](N2C=NC=C2)=[S:20])C=1>C(Cl)Cl>[N:13]([C:6]1[C:7]2[CH:8]=[C:9]([CH3:12])[O:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[C:19]=[S:20]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11095186HCID 11095186, compound

Product 1

HCID 59707357HCID 59707357, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Methoxy-2-methyl-4-nitro-benzofuran (1.24 g, 6.0 mmol) was hydrogenated using Pd/C (10%, dry, 700 mg) and H2 balloon in EtOH (30 mL) at r.t. for 2 h. The reaction mixture was filtered. Purification of the concentrated filtrate by column chromatography (EtOAc:Hexane=2.5:7.5) afforded 7-methoxy-2-methyl-benzofuran-4-ylamine as a brown oil (620 mg, 58%). 7-Methoxy-2-methyl-benzofuran-4-ylamine (620 mg, 3.5 mmol) was dissolved in CH2Cl2 (10 mL). TCDI (thiocarbodiimidazole, 686 mg, 3.9 mmol) was added to the solution and the reaction mixture was stirred at r.t. for 30 min. Silica gel was added to the reaction mixture and the solvent was removed under vacuum. Purification of the silica gel coated crude product by flash column chromatography (EtOAc:Hexane=2:8) afforded the title product as a pale yellow oil (630 mg, 82%).

Workup

  1. additionSilica gel was added to the reaction mixture
  2. customthe solvent was removed under vacuum
  3. customPurification of the silica gel coated crude product by flash column chromatography (EtOAc:Hexane=2:8)

Sources & evidence

ORD record
ord-cc26cee959dc4dd8a1b9502d13896840
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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