Dichloromethane → HCID 4174688, compound

HRID 373585Notes

Reaction equation

HRID 373585 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:22][Cl:23].[CH2:24]([N:26](CC)[CH2:27]C)C>O>[Cl:23][CH2:22][CH2:24][N:26]([CH3:27])[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 8471Triethylamine

Product 1

HCID 4174688HCID 4174688, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

138.95 g (1.85 mol) of 2-(methylamino)ethanol and 500 ml of dichloromethane are introduced into a 2-1 round bottom flask and gaseous hydrochloric acid is bubbled through for two 5-min periods with an interval of 30 min. The solution is partially concentrated and 145 ml (1.98 mol) of thionyl chloride are then added slowly over 1 h 30 min. The mixture is stirred at room temperature for 10 h and is then heated to 50° C. for 2 h. It is allowed to cool, the solvent is evaporated off and the residue is taken up twice with toluene, which is evaporated off. The residue is rinsed with a mixture of diethyl ether and pentane and is dried under vacuum in the presence of phosphorus pentoxide. 230.18 g of 2-chloro-N-methylethanamine hydrochloride are obtained. 46.17 g (355.1 mmol) of this are placed in a 1--1 round bottom flask placed under nitrogen and fitted with a dropping funnel, 100 g (358.7 mmol) of triphenylchloromethane and 400 ml of dichloromethane are added, and 100 ml of triethylamine are introduced slowly. Stirring is continued for 2 days, then water is added, the organic phase is separated off, is washed with water and dried over sodium sulphate and the solvent is evaporated off. The residue is purified by chromatography on a column of silica gel by eluting with a mixture of dichloromethane and cyclohexane and, after recrystallisation from cyclohexane, 79 g of compound are obtained.

Workup

  1. customfitted with a dropping funnel
  2. customthe organic phase is separated off
  3. washis washed with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is evaporated off
  6. customThe residue is purified by chromatography on a column of silica gel
  7. washby eluting with a mixture of dichloromethane and cyclohexane
  8. customafter recrystallisation from cyclohexane, 79 g of compound
  9. customare obtained

Sources & evidence

ORD record
ord-2852ae50242e4188a0d18130fc4a3fb3
Source dataset
uspto-grants-1992_11
Patent number
US05164397

Reaction notes

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