Phenothiazine → Ethyl 3-(diethylamino)propionate

HRID 596461Notes

Reaction equation

HRID 596461 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%

Conditions

Temperature
58 °C

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. customAt the end of this period, unreacted amine was removed by distillation
  4. customThe product was recovered at 80°-81° C.

Sources & evidence

ORD record
ord-bb017c5d72e947eb94998fa93856a5d1
Source dataset
uspto-grants-1977_03
Patent number
US04011223

Reaction notes

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