Triethylamine → HCID 54493867, compound

HRID 329199Notes

Reaction equation

HRID 329199 reaction equation
[P:1](Cl)([O:6][CH2:7][CH3:8])([O:3][CH2:4][CH3:5])=[S:2].[CH:10]1([O:16][C:17]2[S:18][C:19]([C:23]#[N:24])=[C:20]([OH:22])[N:21]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:25](N(CC)CC)C>>[CH:10]([O:6][CH:7]([CH3:8])[CH3:25])([CH3:15])[CH3:11].[CH:10]1([O:16][C:17]2[S:18][C:19]([C:23]#[N:24])=[C:20]([O:22][P:1]([O:6][CH2:7][CH3:8])([O:3][CH2:4][CH3:5])=[S:2])[N:21]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17305O,O-diethyl phosphorochloridothioateHCID 21438990HCID 21438990, compound

Product 2

HCID 7914Diisopropyl EtherHCID 54493867HCID 54493867, compoundYield 80.6%

Procedure

A mixture of 12.44 g of diethyl chlorothiophosphate, 6.67 g of triethylamine and 15 g of 2-cyclohexyloxy-4-hydroxy-5-cyano-thiazole was stirred for 3 days and then concentrated to dryness. The residue was added to water and the aqueous phase was extracted with ether. The ether phase was dried and evaporated to dryness. The residue was crystallized from pentane and then isopropyl ether to obtain 10 g of 2-cyclohexyloxy-4-diethoxythiophosphoryloxy-5-cyano-thiazole in the form of white crystals melting at 58° C.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was added to water
  3. extractionthe aqueous phase was extracted with ether
  4. dry with materialThe ether phase was dried
  5. customevaporated to dryness
  6. customThe residue was crystallized from pentane

Sources & evidence

ORD record
ord-bfcef8c553c8494b9b54268f86762484
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

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