1-Bromohexane → HCID 178444798, compound

HRID 1902644Notes

Reaction equation

[N:1]1[CH2:2][CH2:3][N:4]2[C:8]3[CH:9]=[CH:10][C:11]([NH:13][CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][C:7]=3[S:6][C:5]=12.[H-].[Na+].[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)P(=O)(N(C)C)N(C)C>[Br-:28].[CH2:19]([O:18][C:16]([C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][N:13]([CH2:11][CH2:12][CH2:7][CH2:8][CH2:9][CH3:10])[C:11]1[CH:10]=[CH:9][C:8]2[N:4]3[CH2:3][CH2:2][N+:1]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:5]3[S:6][C:7]=2[CH:12]=1)=[O:17])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of 10 parts of diethyl 2-[(2,3-dihydroimidazo[2,1-b]benzothiazol-7-ylamino)methylene]-propanedioate, 1.1 parts of sodium hydride dispersion 76.8% and 100 parts of hexamethylphosphoric triamide are added 13.2 parts of 1-bromohexane. The whole is stirred over weekend at 50° C. The reaction mixture is poured onto methylbenzene. The latter is washed three times with water, dried, filtered and evaporated. The residue solidifies on triturating in 1,1'-oxbisethane. The product is filtered off and crystallized from 4-methyl-2-pentanone, yielding 4.5 parts of 7-{[2,2-bis(ethoxycarbonyl)ethenyl]hexylamino}-1-hexyl-2,3-dihydroimidazo[2,1-b]benzothiazolium bromide; mp. 162° C.

Workup

additionThe reaction mixture is poured onto methylbenzene
washThe latter is washed three times with water
customdried
filtrationfiltered
customevaporated
customon triturating in 1,1'-oxbisethane
filtrationThe product is filtered off
customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record: ord-f7c11ec36021471ba4e8faffa1e67bfa
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364942

Reaction notes

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