Sodium Carbonate → HCID 54365031, compound

HRID 1419940Notes

Reaction equation

HRID 1419940 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[Cl:31][CH2:32][CH2:33][CH2:34][NH2:35].C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:35][CH2:34][CH2:33][CH2:32][Cl:31])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 738804-(Benzyloxy)benzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 54365031HCID 54365031, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-benzyloxy benzoic acid (5.0 g, 21.9 mmol), 1,1,-carbonyl-diimidazole (3.6 g, 1.05 eq.) and DMF (50 ml) was stirred at 50° C. for 1 h. After cooling to r.t., 3-chloropropylamine hydrochloride (3.4 g, 26.1 mmol) and sodium carbonate (3.5 g, 32.0 mmol) were added and stirring continued for 45 min. After the addition of water, the mixture was extracted with ether. The organic layer was dried (Na2SO4), filtered and evaporated to give 4-benzyloxy-N-(3-chloro-propyl)-benzamide (5.44 g, 85%) as a white solid. MS: me/e=304 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-aa95d60ae82542699415760a7ddd0a9b
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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