1,6-Dibromohexane → (RS)-1-[6-(6-bromo-hexyloxy)-benzo[d]isothiazol-3-yl]-4-methyl-pent-3-en-2-ol

HRID 342200Notes

Reaction equation

HRID 342200 reaction equation
[OH:1][CH:2]([CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]=2[S:6][N:5]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[CH2:26]([NH:29][CH3:30])[CH:27]=[CH2:28]>>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:13][C:11]1[CH:10]=[CH:9][C:8]2[C:4]([CH2:3][CH:2]([OH:1])[CH:14]=[C:15]([CH3:17])[CH3:16])=[N:5][S:6][C:7]=2[CH:12]=1.[CH2:26]([N:29]([CH3:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:13][C:11]1[CH:10]=[CH:9][C:8]2[C:4]([CH2:3][CH:2]([OH:1])[CH:14]=[C:15]([CH3:17])[CH3:16])=[N:5][S:6][C:7]=2[CH:12]=1)[CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 69391N-MethylallylamineHCID 136365324(RS)-3-(2-hydroxy-4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-ol

Product 2

HCID 67596757(RS)-1-[6-(6-bromo-hexyloxy)-benzo[d]isothiazol-3-yl]-4-methyl-pent-3-en-2-olHCID 67684422(RS)-1-[6-[6-(allyl-methyl-amino)-hexyloxy]-benzo[d]isothiazol-3-yl]-4-methyl-pent-3-en-2-ol

Procedure

From (RS)-3-(2-hydroxy-4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-ol (Ex. 7b) with 1,6-dibromohexane and N-allyl-methyl-amine and salt formation (analogously to Ex. 1d) via (RS)-1-[6-(6-bromo-hexyloxy)-benzo[d]isothiazol-3-yl]-4-methyl-pent-3-en-2-ol there is obtained (RS)-1-[6-[6-(allyl-methyl-amino)-hexyloxy]-benzo[d]isothiazol-3-yl]-4-methyl-pent-3-en-2-ol.fumarate (1:1), MS: m/e 403 (M+H+),

Sources & evidence

ORD record
ord-a538a8c006a1445bb76f58e20c998a72
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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