Diethyl Ether → HCID 131710540, compound

HRID 1730914Notes

Reaction equation

HRID 1730914 reaction equation
[C:1]([Cl:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][N:13]([CH3:25])[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.CCOCC>C(Cl)(Cl)Cl>[ClH:11].[CH3:25][N:13]([CH3:12])[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:1](=[O:10])[CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 660233-Phenylprop-2-enoyl chlorideHCID 100584694-(3-(Dimethylamino)propoxy)aniline

Product 1

HCID 131710540HCID 131710540, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 16.6g of cinnamoyl chloride in 125 ml of chloroform is cooled to 15° C and treated dropwise with a solution of 19.4g of 4-[3-(dimethylamino)propoxy]benzenamine in 75 ml of chloroform, keeping the temperature between 15° and 20° C. After stirring for 1 hour, the mixture is heated at reflux for 1 hour, cooled to 25° C and treated with 300 ml of ether to yield 31.6g of material, melting point 253°-257° C, dec.

Workup

  1. customthe temperature between 15° and 20° C
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 1 hour

Sources & evidence

ORD record
ord-7bfbc2f32c2a437384de9314975b53e5
Source dataset
uspto-grants-1976_11
Patent number
US03994900

Reaction notes

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