N-Methylallylamine → (E)-6-(4-bromo-but-2-enyloxy)-3-methyl-benzo[d]isothiazole

HRID 342195Notes

Reaction equation

HRID 342195 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][S:9][C:5]=2[CH:4]=1.[Br:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17]Br.[CH2:19]([NH:22][CH3:23])[CH:20]=[CH2:21]>>[CH3:10][C:7]1[C:6]2[CH:11]=[CH:12][C:3]([OH:2])=[CH:4][C:5]=2[S:9][N:8]=1.[Br:13][CH2:14]/[CH:15]=[CH:16]/[CH2:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][S:9][C:5]=2[CH:4]=1.[CH2:15]([N:22]([CH3:23])[CH2:19]/[CH:20]=[CH:21]/[CH2:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][S:9][C:5]=2[CH:4]=1)[CH:16]=[CH2:17]

Participants

6

Reactant 3

HCID 69391N-MethylallylamineHCID 14316427(1E)-1,4-dibromobut-1-eneHCID 675989146-Methoxy-3-methyl-benzo[d]isothiazole

Product 3

HCID 67597941(E)-6-(4-bromo-but-2-enyloxy)-3-methyl-benzo[d]isothiazoleHCID 67684607(E)-allyl-methyl-[4-(3-methyl-benzo[d]isothiazol-6-yloxy)-but-2-enyl]-amineHCID 1357420033-Methylbenzo[d]isothiazol-6-ol

Procedure

from 6-methoxy-3-methyl-benzo[d]isothiazole (intermediate in Ex. 2d), after cleavage of the methoxy protecting group, reaction with (E)-1,4-dibromobutene and N-allyl-methyl-amine and salt formation, via 3-methyl-benzo[d]isothiazol-6-ol and via (E)-6-(4-bromo-but-2-enyloxy)-3-methyl-benzo[d]isothiazole there is obtained (E)-allyl-methyl-[4-(3-methyl-benzo[d]isothiazol-6-yloxy)-but-2-enyl]-amine.fumarate (1:1), MS: m/e 289 (M+H+),

Sources & evidence

ORD record
ord-c1ff6e3919f443578477174d70354cff
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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