Water → HCID 22105562, compound

HRID 1455977Notes

Reaction equation

HRID 1455977 reaction equation
CI.[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:12]=1[CH2:13][NH:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]=1[OH:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:32](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:12]=1[CH2:13][NH:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]=1[O:26][CH3:32])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22105594HCID 22105594, compound

Product 1

HCID 22105562HCID 22105562, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (2.7 g) was added to a stirred suspension of ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]-3-hydroxybenzoate (6 g) and potassium carbonate (2.6 g) in N,N-dimethylformamide (50 mL) and stirring was continued for 3 hours. The reaction mixture was poured into water (200 mL) and this was extracted three times with diethyl ether (50 mL each time). The combined diethyl ether extracts were washed three times with water (50 mL each time) and dried (MgSO4). The residue obtained on evaporation of the solvent was triturated with petroleum-ether (bp 60-80° C.) to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]-3-methoxybenzoate, yield 5.3 g, mp 78° C.

Workup

  1. extractionthis was extracted three times with diethyl ether (50 mL each time)
  2. washThe combined diethyl ether extracts were washed three times with water (50 mL each time)
  3. dry with materialdried (MgSO4)
  4. customThe residue obtained on evaporation of the solvent
  5. customwas triturated with petroleum-ether (bp 60-80° C.)

Sources & evidence

ORD record
ord-4c6a6bb6718942ffb247a2d1625f1a79
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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