Phosgene → HCID 23324010, compound

HRID 1381281Notes

Reaction equation

HRID 1381281 reaction equation
C(=O)=O.CC(C)=O.[CH3:8][C:9]1[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=1[NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[C:21](Cl)([Cl:23])=[O:22].Cl.CC1C=CC=CC=1NCCC(O)=O>C(Cl)Cl>[Cl:23][C:21]([N:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:10]1[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=1[CH3:8])=[O:22]

Participants

6

Reactant 4

HCID 6371Phosgene2×HCID 24353773-o-Tolylamino-propionic acidHCID 18522661Acetone cardiceHCID 70470725HCID 70470725, compound

Product 1

HCID 23324010HCID 23324010, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a 100 cc round-bottomed flask equipped with magnetic stirring, a thermometer, a dry ice/acetone reflux condenser, a device for introducing gas and a dropping funnel, there is introduced 3-(2-methylanilino)propionic acid (5.29 g; 29.6 mmol) and methylene chloride (30 cc). The mixture maintained under an atmosphere of argon is heated to a temperature in the region of 40° C., and phosgene (5.20 g; 52.6 mmol) is then added with stirring in the course of 25 minutes, while maintaining the temperature between 36° C. and 40° C. During the introduction of phosgene, a white precipitate of 3-(2-methylanilino)propionic acid hydrochloride forms. The reaction mixture is heated to a temperature in the region of 40° C. for a further hour. The white precipitate is then almost completely dissolved. After cooling to 20° C. and the removal of the phosgene which has not reacted, the light precipitate which remains is separated by filtration. The filtrate is concentrated to dryness. N-Chloroformyl-3-(2-methylanilino)propionic acid (7 g) is thus obtained almost pure, m.p. 112° C., the structure of which is confirmed by the infrared spectrum, mass spectrum and proton nuclear magnetic resonance spectrum. The product, after recrystallisation in a toluene/hexane mixture (70:30 by volume), melts at 113° C.

Workup

  1. customIn a 100 cc round-bottomed flask equipped with magnetic stirring
  2. additiona device for introducing gas and a dropping funnel, there
  3. temperatureThe mixture maintained under an atmosphere of argon
  4. additionis then added
  5. temperaturewhile maintaining the temperature between 36° C. and 40° C
  6. dissolutionThe white precipitate is then almost completely dissolved
  7. temperatureAfter cooling to 20° C.
  8. customthe removal of the phosgene which
  9. customhas not reacted
  10. customthe light precipitate which remains is separated by filtration
  11. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-4837ea0be98a4789a5e84da25a5bdd42
Source dataset
uspto-grants-1986_04
Patent number
US04585867

Reaction notes

Loading…