Triethylamine → HCID 18765786, compound

HRID 2104290Notes

Reaction equation

HRID 2104290 reaction equation
Cl.[N+:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:43][O:44][C:45]1[CH:53]=[C:49]([C:50](O)=[O:51])[C:48]([OH:54])=[CH:47][CH:46]=1>ClCCl.O>[OH:54][C:48]1[CH:47]=[CH:46][C:45]([O:44][CH3:43])=[CH:53][C:49]=1[C:50]([NH:11][CH2:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:13][CH:12]=1)=[O:51]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757875-Methoxysalicylic AcidHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 18765786HCID 18765786, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4-nitrophenethylamine hydrochloride (1.81 g; 8.9 mmol), triethylamine (2.8 ml; 20 mmol), hydroxybenzotriazole (1.45 g; 10.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (3.75 g; 19.62 mmol) are added to a solution of 1.5 g (8.9 mmol) of 5-methoxy-salicylic acid in dichloromethane (80 ml). The reaction medium is agitated overnight at 25° C. The mixture is diluted with 40 ml of water and agitated for ten minutes, then the product is extracted with dichloromethane. The organic solution is dried over sodium sulphate, filtered and concentrated under vacuum and the evaporation residue is purified on a silica column (eluent=ethyl acetate/heptane; 50/50) in order to produce a white solid which is obtained with a yield of 64%. Melting point: 200° C.

Workup

  1. stirringagitated for ten minutes
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialThe organic solution is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customthe evaporation residue is purified on a silica column (eluent=ethyl acetate/heptane; 50/50) in order
  7. customto produce a white solid which
  8. customis obtained with a yield of 64%

Sources & evidence

ORD record
ord-cd9741f0d903414a81ebc14913e59441
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

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