Triethylamine → HCID 86759683, compound

HRID 1816684Notes

Reaction equation

HRID 1816684 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)[N:18]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.O[N:51]1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2[N:53]=[N:52]1>ClCCl>[N:51]1([O:27][C:26](=[O:28])[C:25]2[CH:24]=[CH:23][C:22]([C:19]3[N:18]=[C:17]([C:14]4[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:12][CH:13]=4)[O:21][N:20]=3)=[CH:30][CH:29]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2[N:53]=[N:52]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22494663HCID 22494663, compound

Product 1

HCID 86759683HCID 86759683, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[5-[4-(7-methoxy-n-heptyloxy)phenyl]-1,2,4-oxadiazol-3-yl]benzoic acid (2.0 g) and triethylamine (1.1 g) in dichloromethane (60 ml) was added 3-(3-dimethylaminopropyl)-1-ethylcarbodimide hydrochloride (1.4 g) and 1-hydroxybenzotriazole (0.8 g). The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, brine and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure, and the residue was triturated with isopropyl ether. The precipitates were collected by filtration, washed with isopropyl ether and dried to give 4-[5-(4-(7-methoxy-n-heptyloxy)phenyl]-1,2,4-oxadiazol-3-yl]benzoic acid benzotriazol-1-yl ester (2.1 g).

Workup

  1. washThe reaction mixture was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was triturated with isopropyl ether
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with isopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-1ab20f9b23dc430f96c6883e52d2d11d
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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