Formaldehyde → 2-{4-[N-(8-Methoxy-1,2,3,4-tetrahydro-2-naphthyl)-N-propyl-amino]but-2-inyl}-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1494576Notes

Reaction equation

HRID 1494576 reaction equation
[CH2:1]([N:4]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:5]1(=[O:7])=[O:6])[C:2]#[CH:3].[CH3:16][O:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[CH2:26][CH:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:23]2.[CH2:32]=O>O1CCOCC1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[CH2:26][CH:25]([N:28]([CH2:32][C:3]#[C:2][CH2:1][N:4]1[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:5]1(=[O:7])=[O:6])[CH2:29][CH2:30][CH3:31])[CH2:24][CH2:23]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 3909292-(2-Propynyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 127414178-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 141810862-{4-[N-(8-Methoxy-1,2,3,4-tetrahydro-2-naphthyl)-N-propyl-amino]but-2-inyl}-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 75.2%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

2.21 g of propargylsaccharine in 20 ml of dioxane were added dropwise to 2.19 g (10 mmol) of 8-methoxy-2-propylamino-1,2,3,4-tetrahydronaphthalene, 0.36 g (12 mmol) of paraformaldehyde and 0.1 g of copper(II) acetate monohydrate in 10 ml of dioxane at 50° C.. After 5 hours at 80° C., the mixture was freed from solvent. The crude product remaining was purified by flash chromatography on silica gel using toluene/ethyl acetate gradients. 3.4 g (75%) of the title compound were obtained as a solidifying oil.

Workup

  1. customThe crude product remaining was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fa3675b83fbb461b8e4056e5e04f6c9c
Source dataset
uspto-grants-1991_06
Patent number
US05026857

Reaction notes

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