Triethylamine → 3-Chloro-2-(1-ethoxyiminobutyl)-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one

HRID 34427Notes

Reaction equation

HRID 34427 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[C:10](=[O:22])[CH2:11][CH:12]([CH:16]2[CH2:21][CH2:20][CH2:19][S:18][CH2:17]2)[CH2:13][C:14]=1O)[CH2:6][CH2:7][CH3:8])[CH3:2].C(N(CC)CC)C.S(Cl)([Cl:32])=O>O1CCCC1>[Cl:32][C:14]1[CH2:13][CH:12]([CH:16]2[CH2:21][CH2:20][CH2:19][S:18][CH2:17]2)[CH2:11][C:10](=[O:22])[C:9]=1[C:5](=[N:4][O:3][CH2:1][CH3:2])[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 135499147Cycloxydim

Product 1

HCID 544302373-Chloro-2-(1-ethoxyiminobutyl)-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (31 mmol) of 2-(1-ethoxyiminobutyl-3-hydroxy-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one were dissolved in 50 ml of tetrahydrofuran, and 4.7 ml of triethylamine were added, followed by 2.3 ml of thionyl chloride. After 3 hours the resulting precipitate was filtered off with suction, and washed with tetrahydrofuran, and the product-containing filtrate was concentrated. 3-Chloro-2-(1-ethoxyiminobutyl)-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one was obtained as an oil (compound no. 90).

Workup

  1. filtrationAfter 3 hours the resulting precipitate was filtered off with suction
  2. washwashed with tetrahydrofuran
  3. concentrationthe product-containing filtrate was concentrated

Sources & evidence

ORD record
ord-26076139a64545109d2ebff3b9ac8de0
Source dataset
uspto-grants-1988_08
Patent number
US04761486

Reaction notes

Loading…