Triethylamine → HCID 53930965, compound

HRID 582165Notes

Reaction equation

HRID 582165 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:23][C:24]#[C:25][C:26]1[N:30]=[CH:29][N:28]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:27]=1.C(N(CC)CC)C>ClCCl>[Br:1][CH2:23][C:24]#[C:25][C:26]1[N:30]=[CH:29][N:28]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 24408BromineHCID 54249207HCID 54249207, compound

Product 1

HCID 53930965HCID 53930965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of bromine (1.72 ml) in dry dichloromethane (10 ml) was added dropwise to a stirred, cooled (-5° C.), solution of triphenylphosphine (8.74 g) in dry dichloromethane (140 ml) whilst maintaining the temperature below 0° C. The solution was stirred for a further ten minutes at 0° C., then treated dropwise over one hour with a solution of the above alcohol (12.17 g) and triethylamine (4.64 ml) in dry dichloromethane (200 ml). After ten minutes, the mixture was evaporated under reduced pressure and the residue chromatographed on silica, using dichloromethane-ether (25:2) as eluant, to give 1-bromo-3(1-trityl-1,2,4-triazol-3-yl)prop-2-yne (8.10 g, m.p. 181-183° C. dec). NMR (CDCl3): δ 4.1(2H,s), 7.05-7.35(15H,m), 7.95(1H,s). M/S: M+ 427,429.

Workup

  1. temperaturewhilst maintaining the temperature below 0° C
  2. waitAfter ten minutes
  3. customthe mixture was evaporated under reduced pressure
  4. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-ecf9fed3ab944052af1c2c770779f642
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

Loading…