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

HRID 1706791Notes

Reaction equation

HRID 1706791 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.C1C2N(CC#C)C3C(=CC=CC=3)C=2C=CC=1.BrC#CCCCCO.C(O)CCCC#C.Br[O-].[Na+].[CH3:58][N:59]=[C:60]=[O:61]>>[CH3:58][NH:59][C:60]([O:23][CH2:22][CH3:21])=[O:61].[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

7

Reactant 6

HCID 12228Methyl IsocyanateHCID 702345-Hexyn-1-olHCID 2844439-(prop-2-yn-1-yl)-9H-carbazoleHCID 121747156-Bromo-hex-5-yn-1-olHCID 233363449-(N-carbazolyl)-5,7-nonadiyn-1-ol2×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-e0bc1285c5e84291b550a4ede786c987
Source dataset
uspto-grants-1980_06
Patent number
US04208501

Reaction notes

Loading…