Water → HCID 18432353, compound

HRID 2305294Notes

Reaction equation

HRID 2305294 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[C:9]([C:11]1[C:20]([Cl:21])=[C:19]2[C:14]([C:15]([CH3:25])([CH3:24])[CH2:16][CH2:17][S:18]2(=[O:23])=[O:22])=[CH:13][CH:12]=1)=[O:10].[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.O>O1CCCC1>[Cl:21][C:20]1[C:11]([C:9]([C:3]2[C:4](=[O:8])[CH2:5][CH2:6][CH2:7][C:2]=2[S:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:10])=[CH:12][CH:13]=[C:14]2[C:19]=1[S:18](=[O:23])(=[O:22])[CH2:17][CH2:16][C:15]2([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 8471TriethylamineHCID 10927507HCID 10927507, compound

Product 1

HCID 18432353HCID 18432353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

0.7 g (1.75 mmol) of 1-chloro-2-(8-chloro-4,4-dimethyl-1,1-dioxothiochroman-7-yl)carbonylcyclohex-1-en-3-one were dissolved in 10 ml of tetrahydrofuran, and 0.19 g (1.75 mmol) of thiophenol and 0.19 g (1.92 mmol) of triethylamine were added dropwise. The mixture was stirred at 25° C. for two hours and then stirred into water, extracted with ethyl acetate and the organic phases were extracted with 1N hydrochloric acid, dried and concentrated. This gave 0.8 g of beige crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe organic phases were extracted with 1N hydrochloric acid
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8adea02b76b04b1586107a5619d2fd94
Source dataset
uspto-grants-2002_08
Patent number
US06440899B1

Reaction notes

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