Phenothiazine → Ethyl 3-(diethylamino)propionate

HRID 1075776Notes

Reaction equation

HRID 1075776 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH:7]=[CH2:8].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.COC1C=CC(O)=CC=1>>[CH2:1]([N:3]([CH2:8][CH2:7][C:6]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 4

HCID 7108PhenothiazineHCID 8021DiethylamineHCID 8821Ethyl AcrylateHCID 90154-Methoxyphenol

Product 1

HCID 79649Ethyl 3-(diethylamino)propionateYield 96%

Procedure

The following materials were charged to the reaction vessel: anhydrous diethylamine (292 grams); ethyl acrylate (200 grams); phenothiazine (1.0 gram); and p-methoxyphenol (1.0 gram). This mixture was heated at reflux (about 56°-60°C.) for 24 hours. At the end of this period, unreacted amine was removed by distillation. The product was recovered at 80°-81°C. and 10 mm. mercury pressure in a yield of 96 percent. The product is designated herein as Amine Catalyst IX and has the formula, (C2H5)2N-CH2CH2 -C(O)OC2H5, as verified analytically by infrared spectroscopy.

Workup

  1. additionThe following materials were charged to the reaction vessel
  2. temperatureThis mixture was heated
  3. temperatureat reflux (about 56°-60°C.) for 24 hours
  4. customAt the end of this period, unreacted amine was removed by distillation
  5. customThe product was recovered at 80°-81°C.

Sources & evidence

ORD record
ord-e2918e746ada44819f7c7e09103d3c33
Source dataset
uspto-grants-1976_05
Patent number
US03954749

Reaction notes

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