Diethyl Ether → HCID 53874916, compound

HRID 1076088Notes

Reaction equation

HRID 1076088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:13])[CH2:11]Br)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].[OH-].[Na+].CCOCC.[CH:21]([NH2:24])([CH3:23])[CH3:22]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:13])[CH2:11][NH:24][CH:21]([CH3:23])[CH3:22])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 21541803HCID 21541803, compound

Product 1

HCID 53874916HCID 53874916, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

7 g of 1-(3-chloro-4-methylthiophenyl)-2-bromoethanol (0.025 mol) in 50 cc of ethanol are treated with 1.4 g of sodium hydroxide (0.035 mol). The product is stirred for 10 minutes, then diluted with water. One extracts with ether and dries on magnesium sulfate. The solvent is evaporated under vacuum and the residual oil is treated with 100 cc of EtOH and 5.9 g of isopropylamine (0.1 mol). The product is brought to 50° overnight with stirring. The solvent and excess of isopropylamine are evaporated under vacuum. The residual oil crystallises after some time (melting point of 111°-112°C after recrystallisation from cyclohexane). The free base is dissolved in ether; by passing dry gaseous HCl, 4.88 g of 1-(3-chloro-4-methylthiophenyl)-2-isopropylaminoethanol hydrochloride are obtained which are recrystallised from a methanol-ether mixture. Melting point: 139°-141°C.

Workup

  1. customThe solvent is evaporated under vacuum
  2. waitThe product is brought to 50° overnight
  3. stirringwith stirring
  4. customThe solvent and excess of isopropylamine are evaporated under vacuum
  5. customThe residual oil crystallises
  6. customafter some time (melting point of 111°-112°C after recrystallisation from cyclohexane)
  7. dissolutionThe free base is dissolved in ether
  8. customare obtained which
  9. customare recrystallised from a methanol-ether mixture

Sources & evidence

ORD record
ord-d1b5841e71bf4fed9f003ad9453f7a56
Source dataset
uspto-grants-1976_05
Patent number
US03954871

Reaction notes

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