2,2,5,7-Tetramethyl-6-(nitromethylthio)chroman → 5,7-Dimethyl-6-(nitromethylthio)thiachroman

HRID 2081812Notes

Reaction equation

HRID 2081812 reaction equation
C[C:2]1(C)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:18])=[C:7]([S:13][CH2:14][N+:15]([O-:17])=[O:16])[C:8]=2[CH3:12])O1.CC1C(SC#N)=C(C)C=C2C=1CCC[S:26]2>>[CH3:12][C:8]1[C:7]([S:13][CH2:14][N+:15]([O-:17])=[O:16])=[C:6]([CH3:18])[CH:5]=[C:4]2[C:9]=1[CH2:10][CH2:11][CH2:2][S:26]2

Participants

3

Reactant 2

HCID 197807012,2,5,7-Tetramethyl-6-(nitromethylthio)chromanHCID 572339365,7-Dimethyl-6-thiocyanatothiachroman

Product 1

HCID 570022415,7-Dimethyl-6-(nitromethylthio)thiachromanYield 44%

Procedure

Using similar procedures to that described in parts (ii) and (iii) of Example 8, but starting from 5,7-dimethyl-6-thiocyanatothiachroman (J), 5,7-dimethyl-6-(nitromethylthio)thiachroman was obtained in 44% yield as a pale yellow gum which slowly solidified; NMR: 2.17(2H,m), 2.4(3H,s), 2.43(3H,s), 2.69(2H,t), 2.95(2H,m), 5.19(2H,s), 6.91(1H,s).

Sources & evidence

ORD record
ord-39c88442015e4a52b07bef201e76e43f
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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