5-Hexyn-1-ol → 9-(N-carbazolyl)-5,7-nonadiyn-1-ol methylurethane

HRID 1703767Notes

Reaction equation

HRID 1703767 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][C:15]#[C:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1C2[N:35]([CH2:37]C#C)[C:34]3C(=CC=CC=3)C=2C=CC=1.C([OH:46])CCCC#C.Br[O-].[Na+]>>[CH3:34][NH:35][C:37]([O:23][CH2:22][CH3:21])=[O:46].[CH:10]1[C:11]2[N:12]([CH2:14][C:15]#[C:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 702345-Hexyn-1-olHCID 2844439-(prop-2-yn-1-yl)-9H-carbazoleHCID 233363449-(N-carbazolyl)-5,7-nonadiyn-1-ol4×HCID 23673712Sodium hypobromite

Product 1

HCID 867361479-(N-carbazolyl)-5,7-nonadiyn-1-ol methylurethane

Procedure

For example, 9-(N-carbazolyl)-5, 7-nonadiyn -1-ol (5) is synthesized in about 80% yield by cross coupling of 3-(N-carbazolyl)-1-propyne (3) with 6-bromo-5-hexyn-1-ol (6), which, in turn, is synthesized from 5-hexyn-1-ol with sodium hypobromite. Reaction of (5) with methylisocyanate (7) gives 9-(N-carbazolyl)- 5,7-nonadiyn-1-ol methylurethane (8) in almost quantitative yield. ##STR12##

Sources & evidence

ORD record
ord-b0880f5d32284a6d846c55228c11f369
Source dataset
uspto-grants-1978_11
Patent number
US04125534

Reaction notes

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