Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → 4-Amino-3,5-dichloro-alpha-[[[4-[2-[(2-phenylethyl)thio]ethoxy]butyl]amino]methyl]benzenemethanol

HRID 2108139Notes

Reaction equation

HRID 2108139 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][NH2:12])[OH:10])=[CH:4][C:3]=1[Cl:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][S:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH:9]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][S:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[OH:10])=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 23045275[2-[[2-(4-Bromobutoxy)ethyl]thio]ethyl]benzene

Product 1

HCID 230453134-Amino-3,5-dichloro-alpha-[[[4-[2-[(2-phenylethyl)thio]ethoxy]butyl]amino]methyl]benzenemethanolYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-α-(aminomethyl)-3,5-dichlorobenzenemethanol (1.53 g), [2-[[2-(4-bromobutoxy)ethyl]thio]ethyl]benzene (1.0 g) and DEA (0.71 g) in DMF (20 ml) was stirred under nitrogen at 100° for 2 h. The solvent was evaporated in vacuo and the residue purified by FCC eluting with System G (95:5:1) to give an oil. The oil was partitioned between dichloromethane (50 ml) and 8% sodium bicarbonate (75 ml) and the aqueous solution re-extracted with dichloromethane (50 ml). The organic extracts were dried and evaporated in vacuo to give the title compound (924 mg,) as a white solid m.p. 74°-77°.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified by FCC
  3. washeluting with System G (95:5:1)
  4. customto give an oil
  5. customThe oil was partitioned between dichloromethane (50 ml) and 8% sodium bicarbonate (75 ml)
  6. extractionthe aqueous solution re-extracted with dichloromethane (50 ml)
  7. customThe organic extracts were dried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5c91297f039f42448e036148e70f5449
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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