3-Isothiocyanato-4-methylthiophene → HCID 22139854, compound

HRID 2250498Notes

Reaction equation

HRID 2250498 reaction equation
[N:1]([C:4]1[C:8]([CH3:9])=[CH:7][S:6][CH:5]=1)=[C:2]=[S:3].[O:10]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[NH2:20])[O:13][CH2:12][CH2:11]1>O1CCCC1>[O:10]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[NH:20][C:2]([NH:1][C:4]2[C:8]([CH3:9])=[CH:7][S:6][CH:5]=2)=[S:3])[O:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 221398273-Isothiocyanato-4-methylthiopheneHCID 22139851HCID 22139851, compound

Product 1

HCID 22139854HCID 22139854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-isothiocyanato-4-methylthiophene (296.2 mg, see example 1a) in absolute tetrahydrofuran (10 ml) was added dropwise to a solution of 1,4-dioxaspiro[4.5]dec-6-ylamine (300 mg) in absolute tetrahydrofuran (10 ml), the mixture was stirred at room temperature for 2 hours and the solvent was then removed under reduced pressure. The residue was purified by preparative chromatography and the product-containing fractions were combined, freed from acetonitrile, made basic and extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. This gave 428 mg of the desired product.

Workup

  1. customthe solvent was then removed under reduced pressure
  2. customThe residue was purified by preparative chromatography
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7d1a3db3229f465ab7e594b22fe34b82
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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