Formaldehyde → (N-benzylglycylmethyl)hydroxymethylphosphinic acid

HRID 224522Notes

Reaction equation

HRID 224522 reaction equation
[OH:1][CH2:2][P:3]([OH:5])[OH:4].Cl.[CH2:7]([NH:14][CH2:15][C:16]([OH:18])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:19]=O>Cl>[CH2:7]([NH:14][CH2:15][C:16]([CH2:19][P:3]([CH2:2][OH:1])(=[O:5])[OH:4])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2756624N-Benzylglycine HydrochlorideHCID 23330988Hydroxymethylphosphonous acid

Product 1

HCID 54414086(N-benzylglycylmethyl)hydroxymethylphosphinic acidYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The procedure of Example 1 is carried out starting from 9.6 g (0.1 mole) of hydroxymethylphosphonous acid ##STR8## 20.2 g (0.1 mole) of N-benzylglycine hydrochloride, 100 ml of conc. hydrochloric acid and 31.6 g of 38% formaldehyde solution. The reaction mixture is concentrated by rotary evaporation, yielding 22.7 g (88%) of (N-benzylglycylmethyl)hydroxymethylphosphinic acid of the formula ##STR9## as a glassy substance which sinters at 92° C., becomes liquid at 118° C., and decomposes at 135° C.

Workup

  1. concentrationThe reaction mixture is concentrated by rotary evaporation

Sources & evidence

ORD record
ord-26e3264fcbf5468f95067205d987fe19
Source dataset
uspto-grants-1980_11
Patent number
US04233056

Reaction notes

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