Dichloromethane → HCID 87623974, compound

HRID 2382230Notes

Reaction equation

HRID 2382230 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@@H:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[OH:6].C(Cl)Cl.O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](O)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CO>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:6][C@H:5]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3][NH:2][CH3:1])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 100950473-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-

Product 1

HCID 87623974HCID 87623974, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (S)-3-methylamino-1-thiophen-2-yl-propan-1-ol (5.0 g, 29.2 mmol), methylene chloride (50 mL), p-toluenesulfonic acid hydrate (5.55 g, 29.2 mmol) and methanol (20 mL) is stirred 1 h at 25° C., then concentrated to dryness. The residue (10.8 g) which solidifies after a few hours is finally recrystallised from butanol (30 mL) affording a white powder (6.0 g, 60%); 1H-NMR (DMSO-d6, 400 MHz): 8.1 (1H, s, broad), 7.5 (2H, dm), 7.42 (1H, dd), 7.1 (2H, dm), 7.0 (2H, m), 4.92 (1H, dd), 2.97 (2H, m, symm.), 2.57 (3H, s), 2.28 (3H, s), 2.0 (2H, m); 13C-NMR (DMSO-d6, 100 MHz): 149.3, 145.5, 137.6, 128.0, 126.6, 125.4, 124.4, 123.0, 66.1, 45.8, 35.1, 32.7, 20.7.

Workup

  1. concentrationconcentrated to dryness
  2. waitThe residue (10.8 g) which solidifies after a few hours
  3. customis finally recrystallised from butanol (30 mL)

Sources & evidence

ORD record
ord-53c8f074c2c541ffbb791562f68f5a86
Source dataset
uspto-grants-2012_09
Patent number
US08258338B2

Reaction notes

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