1-Hydroxybenzotriazole → HCID 22101906, compound

HRID 1458292Notes

Reaction equation

HRID 1458292 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:43][CH:44]1[CH2:48][N:47]([CH2:49][CH3:50])[N:46]([CH2:51][CH3:52])[CH2:45]1>ClCCl>[CH2:51]([N:46]1[CH2:45][CH:44]([NH:43][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])[CH2:48][N:47]1[CH2:49][CH3:50])[CH3:52]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53471241HCID 53471241, compound

Product 1

HCID 22101906HCID 22101906, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-geranyloxybenzoic acid (1.36 g) was dissolved in dichloromethan (20 ml) and 1-hydroxybenzotriazole (0.80 g) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.14 g) were added thereto while being cooled with ice. After the resulting mixture was stirred for 30 minutes, 4-amino-1,2-diethyl pyrazolidine (0.71 g) was added thereto and the mixture was stirred for one night at room temperature. The reaction liquid was washed with brine and then dried over sodium sulfite anhydride. Thereafter, the solvent was evaporated under a vacuum. The residue was purified by silica gel column-m chromatography (chloroform:methanol=30:1), thereby yielding 1.71 g (87%) of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringthe mixture was stirred for one night at room temperature
  3. customThe reaction liquid
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfite anhydride
  6. customThereafter, the solvent was evaporated under a vacuum
  7. customThe residue was purified by silica gel column-m chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-e99ccb1cacd949e393c4609300a762f7
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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