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 258418Notes

Reaction equation

HRID 258418 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-c12c3eef326b4ef590e859ef8798a42b
Source dataset
uspto-grants-1993_11
Patent number
US05266709

Reaction notes

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