Chloroform → HCID 54361201, compound

HRID 249373Notes

Reaction equation

HRID 249373 reaction equation
[CH3:1][S:2][CH3:3].[SH:4][CH2:5][CH2:6][S:7][CH2:8]CS.C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>O>[CH3:1][S:2][CH2:3][CH2:8][S:7][CH2:6][CH2:5][S:4][C:22](=[O:25])[CH:23]=[CH2:24]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 86746873HCID 86746873, compound

Product 1

HCID 54361201HCID 54361201, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Three-necked flask fitted with a thermometer, a stirrer and a dropping funnel was charged with 16.8 g (0.10 mole) of di(2-mercaptoethyl)sulfide monomethyl thioether, 11.1 g (0.11 mole) of triethylamine, and 100 ml of anhydrous chloroform, and the mixture was cooled to 0° C. With stirring, 10.0 g (0.11 mole) of acryloyl chloride was gradually added dropwise. At this time, the reaction temperature was maintained at 0° to 5° C. After the end of addition, the mixture was further stirred at 20° C. for 1 hour. Then, the reaction mixture was poured into water. The organic layer was washed with a dilute aqueous solution of sodium carbonate, and then with water. The organic layer was dried over anhydrous magnesium sulfate. The resulting oil was purified by column chromatography (filler: silica gel; developing agent: chloroform) to give 23.1 g of acryloylthioethyl 2-methylthioethyl sulfide as a colorless clear oil. This compound had a refractive index of 1.585. In its IR spectrum, a strong absorption based on the carbonyl group at 1765 cm-1 and an absorption based on the terminal double bond at 1640 cm-1 were observed. Its elemental analysis values (the parenthesized values were calculated values) well agreed with the calculated values. C: 43.26 % (43.21%), H: 6.58% (6.36%), S: 42.98% (43.26%).

Workup

  1. customThree-necked flask fitted with a thermometer, a stirrer and a dropping funnel
  2. temperatureAt this time, the reaction temperature was maintained at 0° to 5° C
  3. additionAfter the end of addition
  4. stirringthe mixture was further stirred at 20° C. for 1 hour
  5. washThe organic layer was washed with a dilute aqueous solution of sodium carbonate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customThe resulting oil was purified by column chromatography (filler: silica gel; developing agent: chloroform)

Sources & evidence

ORD record
ord-525ec8dfe58d410282d8a1f41992fafe
Source dataset
uspto-grants-1993_05
Patent number
US05214116

Reaction notes

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