Diethyl chlorophosphate → HCID 86745260, compound

HRID 1460151Notes

Reaction equation

HRID 1460151 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)=[NH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[P:34](Cl)([O:39][CH2:40][CH3:41])([O:36][CH2:37][CH3:38])=[O:35]>C(Cl)Cl>[C:1]1([NH:7][C:8](=[N:9][P:34](=[O:35])([O:39][CH2:40][CH3:41])[O:36][CH2:37][CH3:38])[NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 178511996HCID 178511996, compound

Product 1

HCID 86745260HCID 86745260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2.94 g (10 mmol) of 1-phenyl-3-(4-phenyl-2-thiazolyl) guanidine (dried at 110° C./0.1 mm) in 150 ml of methylene chloride was allowed to react with 2.03 g (10 mmol) of N,O-bis(trimethylsilyl) acetamide and 1.73 g (10 mmol) of diethyl chlorophosphate for 3 months by the procedure of Example 4. The reaction mixture was evaporated to dryness then was subjected to "dry column" chromatography (method of B. Loev and M. M. Goodman, Chem. and Industry, 2026 (1967) on 500 g of silica gel, and developed with 700 ml of methylene chloride-ethyl acetate, 9/1 (v/v). A band in the Nylon® column at Rf 0.25-0.4, visualized as a dark band under ultraviolet light at 254 nm, was cut out, and extracted with chloroform-methanol, 3/1 (v/v). Evaporation of the extracts left 1.35 g of product as a pale yellow, thick syrup; NMR (CDCl3, 80 MHz) δ 1.37 (t, 6H, CH3), δ 4.11(5 peaks, 4H, OCH2), 6.98 (s, 1H, =CH--S), 7.35(m, 10H, aromatic); IR (neat) 1653 (C=N) and 1032 cm-1 (P=O); TLC (SiO2, CHCl3 --MEOH, 19/1 (v/v)) showed only one spot under UV light.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customdry column" chromatography (method of B
  3. extractionextracted with chloroform-methanol, 3/1 (v/v)
  4. customEvaporation of the extracts
  5. waitleft 1.35 g of product as a pale yellow, thick syrup

Sources & evidence

ORD record
ord-afe5a4228dca4e36a6959c725d097b0a
Source dataset
uspto-grants-1991_12
Patent number
US05070082

Reaction notes

Loading…