Acetic Acid → HCID 23337312, compound

HRID 903013Notes

Reaction equation

HRID 903013 reaction equation
[CH2:1]([CH:5](C(O)=O)[N:6](C(OCC1C=CC=CC=1)=O)[CH2:7][P:8]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:9])[CH2:2][CH2:3]C.Br.C(OCC)C.[C:41]([OH:44])(=[O:43])[CH3:42]>>[CH2:5]([N:6]([CH2:7][P:8]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:9])[CH2:42][C:41]([OH:44])=[O:43])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 3283Diethyl Ether2×HCID 131711908HCID 131711908, compound

Product 1

HCID 23337312HCID 23337312, compound

Procedure

n-Butyl N-carbobenzoxy-N-[bis(pentylthio)phosphinylmethyl]glycine (5.5 g., 0.01 mole) was reacted with 32% hydrogen bromide (15 ml) in glacial acetic acid at 0° C. Diethyl ether was added and the oily precipitate isolated by decantation of the ether layer. The oil was washed twice with ether, suspended in benzene and then treated with propylene oxide. The resulting solution was concentrated in vacuo to yield n-butyl N-[bis(pentylthio)phosphinylmethyl]-glycine (0.7 g., 0.002 mole) as an oil, ND27 =1.4905.

Workup

  1. washThe oil was washed twice with ether
  2. additiontreated with propylene oxide
  3. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-0ee47fe05e2c4968bd731ec65b9171e5
Source dataset
uspto-grants-1980_10
Patent number
US04226611

Reaction notes

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