1-Methylimidazole → HCID 66680548, compound

HRID 1626738Notes

Reaction equation

HRID 1626738 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[O:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[O:21][CH2:22][C:23]([OH:25])=O)=[CH:14]1.[NH2:29][C:30]1[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][C:31]=1[C:32]([O:34][CH3:35])=[O:33].ON1C2C=CC=CC=2N=N1.CN1C=CN=C1>O.CC(N(C)C)=O>[Br:40][C:37]1[CH:38]=[CH:39][C:30]([NH:29][C:23](=[O:25])[CH2:22][O:21][C:20]2[CH:26]=[CH:27][CH:28]=[C:18]([C:15]3[CH:16]=[CH:17][O:13][CH:14]=3)[CH:19]=2)=[C:31]([CH:36]=1)[C:32]([O:34][CH3:35])=[O:33]

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 757711-HydroxybenzotriazoleHCID 736224Methyl 2-amino-5-bromobenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66680112HCID 66680112, compound

Product 1

HCID 66680548HCID 66680548, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Under ice-cooling, 1.53 g (7.97 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a DMAc (5 mL) solution comprising 1.45 g (6.64 mmol) of [3-(furan-3-yl)phenoxy]acetic acid, 1.60 g (6.97 mmol) of methyl 2-amino-5-bromobenzoate, and 1.08 g (7.97 mmol) of 1-hydroxybenzotriazole, and the mixture was stirred at room temperature for 4 hours. Under ice-cooling, 1.63 g (19.9 mmol) of 1-methylimidazole was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was stirred for 1 hour. The precipitates were collected by filtration and washed with water and IPE, followed by drying under reduced pressure at 50° C. for 3 hours, thereby giving 2.30 g of methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 81%).

Workup

  1. temperatureUnder ice-cooling
  2. temperatureUnder ice-cooling
  3. stirringthe mixture was stirred at room temperature overnight
  4. stirringthe mixture was stirred for 1 hour
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water and IPE
  7. customby drying under reduced pressure at 50° C. for 3 hours

Sources & evidence

ORD record
ord-ec82b77a04664b03a3db505c70407137
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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