2-Amino-2-methyl-1-propanol → HCID 23316756, compound

HRID 1982485Notes

Reaction equation

HRID 1982485 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([OH:10])=O.[NH2:11][C:12]([CH3:16])([CH3:15])[CH2:13]O>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:13][C:12]1([CH3:16])[CH2:15][O:10][CH:8]([C:4]2[S:5][CH:6]=[CH:7][C:3]=2[O:2][CH3:1])[NH:11]1

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 14834753-Methoxythiophene-2-carboxylic acid

Product 1

HCID 23316756HCID 23316756, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

50.2 g (0.32 moles) of 3-methoxy-2-thiophene carboxylic acid are refluxed in 300 ml of thionyl chloride for 2 hours, the reaction solution is evaporated in vacuo, the crystalline residue (56 g) is dissolved in 250 ml of methylene chloride and added dropwise with stirring to a solution of 57 g (0.64 moles) of 2-amino-2-methyl-1-propanol in 200 ml of methylene chloride at 0° C. within 1/2 hour. After 12 hours of stirring at room temperature, the solution is concentrated under vacuum, cooled, the precipitate is aspirated, washed well with water, dried, 135 ml of thionyl chloride are added slowly with cooling, and the solution is stirred at room temperature for 12 hours. Then it is evaporated in vacuo, the residue is dissolved in water, extracted with ether, the aqueous phase is made alkaline with aqueous 2N sodium hydroxide and extracted several times with methylene chloride. The combined methylene chloride phases are dried with sodium sulfate and evaporated in vacuo. Yield: 57.0 g (84%), m.p. (petroleum ether) 97°-98° C.

Workup

  1. customthe reaction solution is evaporated in vacuo
  2. dissolutionthe crystalline residue (56 g) is dissolved in 250 ml of methylene chloride
  3. additionadded dropwise
  4. concentrationthe solution is concentrated under vacuum
  5. temperaturecooled
  6. washwashed well with water
  7. customdried
  8. addition135 ml of thionyl chloride are added slowly
  9. temperaturewith cooling
  10. stirringthe solution is stirred at room temperature for 12 hours
  11. customThen it is evaporated in vacuo
  12. dissolutionthe residue is dissolved in water
  13. extractionextracted with ether
  14. extractionextracted several times with methylene chloride
  15. dry with materialThe combined methylene chloride phases are dried with sodium sulfate
  16. customevaporated in vacuo
  17. customYield: 57.0 g (84%), m.p. (petroleum ether) 97°-98° C.

Sources & evidence

ORD record
ord-e71b554a531541febfe543c67e639915
Source dataset
uspto-grants-1986_06
Patent number
US04596830

Reaction notes

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