Dichloromethane → n-butyl N-carbobenzoxy-N-[di-(n-pentylthio)phosphonomethyl]glycinate

HRID 224226

Reaction equation

HRID 224226 reaction equation
[C:1]([N:11]([CH2:20][P:21]([O:25]Cl)([O:23]Cl)=[O:22])[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:27]([SH:32])[CH2:28][CH2:29][CH2:30][CH3:31].C(Cl)Cl>C(OCC)C.C(N(CC)CC)C>[C:1]([N:11]([CH2:20][P:21]([O:25][S:32][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([O:23][S:32][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:22])[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 80671-PentanethiolHCID 53954703Butyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 23332174n-butyl N-carbobenzoxy-N-[di-(n-pentylthio)phosphonomethyl]glycinate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Procedure

Butyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate (13.25 g., 0.34 mole) and pentanethiol (6.96 g., 0.67 mole) were dissolved in 100 ml. of diethyl ether and 50 ml. of methylene chloride. Triethylamine (6.76 g) dissolved in 100 ml. of diethyl ether was then added. The reaction mixture was stirred for 16 hours at ambient temperatures and then filtered. The filtrate was washed with 3% ammonium hydroxide, then with brine, then with 5% hydrochloric acid and then the brine and the ether solution dried over sodium sulfate and then evaporated in vacuo to yield a crude product. The crude product was chromatographed through a silica gel column employing methylene chloride as the eluant. Evaporation of the methylene chloride yielded n-butyl N-carbobenzoxy-N-[di-(n-pentylthio)phosphonomethyl]glycinate as a yellow oil, ND25 =1.5218 and having the following analysis.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 3% ammonium hydroxide
  3. dry with materialwith brine, then with 5% hydrochloric acid and then the brine and the ether solution dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto yield a crude product
  6. customThe crude product was chromatographed through a silica gel column
  7. customEvaporation of the methylene chloride

Sources & evidence

ORD record
ord-f29f66b2674b4a5882bec67865d02067
Source dataset
uspto-grants-1980_11
Patent number
US04231782

Linked notes

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