Benzoyl isothiocyanate → 1-[2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethyl]-3-benzoylthiourea

HRID 1681293Notes

Reaction equation

HRID 1681293 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][C:15]1([CH3:29])[O:20][C:19]2[C:21]([CH3:28])=[C:22]([CH3:27])[C:23]([OH:26])=[C:24]([CH3:25])[C:18]=2[CH2:17][CH2:16]1>CC(C)=O>[OH:26][C:23]1[C:22]([CH3:27])=[C:21]([CH3:28])[C:19]2[O:20][C:15]([CH2:14][CH2:13][NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:11])([CH3:29])[CH2:16][CH2:17][C:18]=2[C:24]=1[CH3:25]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 200967022-(2-aminoethyl)-2,5,7,8-tetramethyl-6-hydroxy-3,4-dihydro-2H-benzo[1,2-b]pyran

Product 1

HCID 224173891-[2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethyl]-3-benzoylthioureaYield 56.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of benzoylisothiocyanate (28.0 g) in acetone (200 ml) was added dropwise to a solution of amine (prepared in reference example 3, 34.3 g) in acetone (800 ml). The solution was stirred for 15 hours at room temperature. The reaction solution was evaporated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1→4:1→2:1) to give the title compound (32.0 g) having the following physical data.

Workup

  1. customThe reaction solution was evaporated
  2. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1→4:1→2:1)

Sources & evidence

ORD record
ord-25dd307fd9b9413e89f88fa80eef78cd
Source dataset
uspto-grants-1992_12
Patent number
US05169957

Reaction notes

Loading…