Water → HCID 19920043, compound

HRID 1648667Notes

Reaction equation

HRID 1648667 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].[OH-:25].[Na+].[OH2:27]>CC(N(C)C)=O>[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:12](=[O:27])[C:11]2[CH:10]=[CH:9][C:8]([O:25][C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 16402HexamethylenediamineHCID 741934-Phenoxybenzoyl chloride

Product 1

HCID 19920043HCID 19920043, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
100 °C

Procedure

p-Phenoxybenzoyl chloride (36.77g, 0,158 mole) was added at room temperature to a stirred solution of hexamethylene diamine (8.75 g, 0.075 mole) in DMAc (230 mL). The temperature of the reaction mixture rose to about 75° C. and a white precipitate formed. After standing overnight the mixture was heated at 100° C. for 1 hour, allowed to cool then poured into a stirred mixture of 200 mL sodium hydroxide (1N) and water (1 L). The product 1,6-bis-(4-phenoxybenzamido)-n-hexane (28.3 g, 74% yield) was recrystallized from a mixture of 200 mL denatured alcohol and 150 mL DMAc, filtered, washed with denatured alcohol, and dried under vacuum at 140° C. for 6 hours. The DSC purity was 99.91%, mp 183°-184.3° C.

Workup

  1. customrose to about 75° C.
  2. customa white precipitate formed
  3. temperatureto cool

Sources & evidence

ORD record
ord-c2eee80efb124492a891d1dcfc7fe890
Source dataset
uspto-grants-1995_07
Patent number
US05436310

Reaction notes

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