Triethylamine → HCID 22341476, compound

HRID 584998Notes

Reaction equation

HRID 584998 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5](O)=[O:6].[CH2:12]([N:14](CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([NH:14][CH3:12])=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 51825203-Bromo-5-iodobenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 22341476HCID 22341476, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

37.5 g (115 mmol) of 3-bromo-5-iodobenzoic acid in 300 ml of dimethylformamide are introduced into a round-bottomed flask under a stream of nitrogen. 17.6 ml (127 mmol) of triethylamine, 17 g (126 mmol) of 1-hydroxybenzotriazole and 7.75 g (115 mmol) of methylamine hydrochloride are added. The reaction medium is cooled to 0° C., followed by portionwise addition of 24.2 g (126 mmol) of 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride. The medium is allowed to warm to room temperature and is stirred for 18 hours. It is then poured into water and the precipitate obtained is filtered off, washed with heptane and then dried. 37.3 g (96%) of the expected product are obtained in the form of a beige-colored powder with a melting point of 205° C.

Workup

  1. temperatureto warm to room temperature
  2. customthe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with heptane
  5. customdried

Sources & evidence

ORD record
ord-056323976f24450392432941d285bfa7
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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