Ethanol → HCID 86736994, compound

HRID 1395543Notes

Reaction equation

HRID 1395543 reaction equation
S(Cl)([Cl:3])=O.C[CH2:6][CH:7]([NH:9][CH:10]([CH3:12])[CH3:11])O.C(O)C.[CH:16]([Cl:19])(Cl)Cl>>[ClH:3].[CH3:6][CH:7]([NH:9][CH:10]([CH3:12])[CH3:11])[CH2:16][Cl:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 20572331HCID 20572331, compound

Product 1

HCID 86736994HCID 86736994, compound

Procedure

Thionyl chloride (57 ml. 0.775 M) is added with stirring and cooling (below 20°) to a solution of 2-methylisopropylaminoethanol (75 g., 0.64 M) dissolved in chloroform (300 ml.). The temperature is raised to 45° at which point gas evolution becomes evident and is maintained at 45°-55° for 11/2 hour. The reaction mixture is refluxed for 2 hours. Then the mixture is cooled to 25° and ethanol (25 ml.) is added with stirring and the mixture is concentrated under vacuum. The residue is taken up in isopropanol (50 ml.) and ether (350 ml.) is added. The product is filtered and on drying, weights 107 g., melting point 114°-117°.

Workup

  1. temperatureThe temperature is raised to 45° at which point gas evolution
  2. temperatureis maintained at 45°-55° for 11/2 hour
  3. temperatureThe reaction mixture is refluxed for 2 hours
  4. temperatureThen the mixture is cooled to 25°
  5. stirringwith stirring
  6. concentrationthe mixture is concentrated under vacuum
  7. additionether (350 ml.) is added
  8. filtrationThe product is filtered
  9. customon drying

Sources & evidence

ORD record
ord-618ad43b1ccb4d07b44f16470b767941
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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