Methyl Acrylate → HCID 14011705, compound

HRID 1651028Notes

Reaction equation

HRID 1651028 reaction equation
[CH:1]1([NH:7][CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13]C)(=O)[CH:10]=[CH2:11].[P:15]([OH:18])([OH:17])[OH:16].P(Cl)(Cl)Cl>C1(C)C=CC=CC=1.O.CC(C)=O>[CH:1]1([N:7]([CH2:11][CH2:10][C:9]([OH:13])([P:15]([OH:18])(=[O:16])[OH:17])[P:15]([OH:18])(=[O:17])[OH:16])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 7514N-MethylcyclohexylamineHCID 24387Phosphorus trichlorideHCID 107909Phosphorous acid

Product 1

HCID 14011705HCID 14011705, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

15 g. 3-N-Cyclohexyl-N-methylaminopropionic acid (prepared from N-cyclohexyl-N-methylamine (commercially available) and methyl acrylate in toluene; yield of ester 76% of theory, m.p. 131°-134° C., yield of acid 92% of theory, m.p. 101°-105° C.) are heated to 80° C. with 13.3 g. phosphorous acid. The melt is mixed with 14.1 ml. phosphorus trichloride and kept at the same temperature for 16 hours. 240 ml. water are then added thereto and the reaction mixture is stirred for 1 day at 100° C. It is then filtered, the filtrate is concentrated in a vacuum and the oil obtained is poured into 1 litre of acetone, crystallisation thereby commencing. The crystals are dissolved in water and purified by ion exchanger chromatography in the manner described in Example 1. Yield 4.5 g. (16.9% of theory) as monohydrate; m.p. 142° C. with sintering, 182° C. (decomp.); Mrel =0.3.

Workup

  1. additionThe melt is mixed with 14.1 ml
  2. filtrationIt is then filtered
  3. concentrationthe filtrate is concentrated in a vacuum
  4. customthe oil obtained
  5. custompurified by ion exchanger chromatography in the manner

Sources & evidence

ORD record
ord-3c5863944e6741f88be32de40b2c3e08
Source dataset
uspto-grants-1990_05
Patent number
US04927814

Reaction notes

Loading…