Hydrochloric Acid → ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

HRID 224223Notes

Reaction equation

HRID 224223 reaction equation
C(N(CP(O)(O)=O)CC(O)=O)C.[Cl:13]C(OCC1C=CC=CC=1)=O.C(=O)([O-])[O-].[Na+].[Na+].[ClH:30].[C:31]([N:41]([CH2:48][P:49]([OH:52])([OH:51])=[O:50])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>O>[C:31]([N:41]([CH2:48][P:49]([O:51][Cl:13])([O:52][Cl:30])=[O:50])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2×HCID 15029720Ethyl N-phosphonomethylglycineHCID 23337289ehtyl N-carbobenzoxy-N-phosphonomethylglycinate

Product 1

HCID 54297302ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl N-phosphonomethylglycine (9.85 g., 0.05 mole) and benzyl chloroformate (9.4 g., 0.05 mole) were dissolved in 50 ml. of water and sodium carbonate (7.95 g., 0.075 mole) was added over a 1/2 hour period. The solution was stirred until all of the benzyl chloroformate had reacted. Concentrated hydrochloric acid (12.5 ml) was then added. Upon standing ehtyl N-carbobenzoxy-N-phosphonomethylglycinate separated as an oil. The oil was then dried in a vacuum dessicator over phosphorus pentoxide at 0.55 torr. A 4 g. sample of the oil was dissolved in oxalyl chloride (20 ml) and stirred until gas evolution ceased. The mixture was concentrated in vacuo to yield ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate as a colorless oil. Other ester derivative starting materials for use in the production of the compounds of this invention are prepared by the same procedure employing the appropriate ester of N-phosphonomethylglycine. These derivatives were employed to produce the compounds in accordance with the following examples.

Workup

  1. customhad reacted
  2. customseparated as an oil
  3. dry with materialThe oil was then dried in a vacuum dessicator over phosphorus pentoxide at 0.55 torr
  4. dissolutionsample of the oil was dissolved in oxalyl chloride (20 ml)
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-9cfd705ddddf4242a074179f6ef59136
Source dataset
uspto-grants-1980_11
Patent number
US04231782

Reaction notes

Loading…