Acetic Acid → HCID 70582843, compound

HRID 2057498Notes

Reaction equation

HRID 2057498 reaction equation
C([CH:3]([C:34]([OH:36])=[O:35])[N:4]([CH2:15][P:16]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)=[S:17])[C:5](OCC1C=CC=CC=1)=O)C.Br.[C:38](O)(=O)C>>[CH2:5]([N:4]([CH2:15][P:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)=[S:17])[CH2:3][C:34]([OH:36])=[O:35])[CH3:38]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20330646HCID 20330646, compound

Product 1

HCID 70582843HCID 70582843, compound

Procedure

Ethyl-N-[bis(metachlorophenoxy)phosphinothioylmethyl]-N-(benzyloxycarbonyl)glycine (1.0 g.) was dissolved in 15 ml. of 35% hydrobromic acid in acetic acid and was stirred for one hour. The reaction mixture was concentrated under vacuum and the residue triturated thoroughly with ether three times, dissolved in benzene and treated with excess propylene oxide. The resultant solution was concentrated in vacuo and the residue chromatographed on silica gel using diethyl ether as an eluant to yield ethyl-N-[bis(metachlorophenoxy)phosphinothioylmethyl]glycine as an oil, ND25 =1.5371, which gave the following analysis.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue triturated thoroughly with ether three times
  3. dissolutiondissolved in benzene
  4. additiontreated with excess propylene oxide
  5. concentrationThe resultant solution was concentrated in vacuo
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-0a45c7a0e12146bb96c716c53a1aaaeb
Source dataset
uspto-grants-1980_07
Patent number
US04211548

Reaction notes

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