4-Toluenesulfonyl chloride → HCID 131733532, compound

HRID 2284385Notes

Reaction equation

HRID 2284385 reaction equation
ClC1C=C(N(C)C[C:11](=O)[CH2:12][C:13](OCC)=[O:14])C=C(Cl)C=1.[OH:20][CH2:21][CH2:22][NH:23][NH2:24].C(N(CC)CC)C.[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>CCO.C(OCC)(=O)C>[OH:20][CH2:21][CH2:22][N:23]1[CH:11]=[CH:12][C:13](=[O:14])[N:24]1[S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 80172-HydrazinoethanolHCID 8471TriethylamineHCID 57382355HCID 57382355, compound

Product 1

HCID 131733532HCID 131733532, compoundYield 141.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-((3,5-dichlorophenyl)(methyl)amino)-3-oxobutanoate (304 mg, 1.0 mmol) in EtOH (5 mL), was added 2-hydroxyethylhydrazine (85 uL, 1.1 mmol) and was stirred for 3 h. After the volatiles were evaporated, the residue was dissolved in dry acetonitrile (10 mL) and triethylamine (156 uL, 1.1 mmol) followed by the addition of tosyl chloride (190 mg, 1.0 mmol). The solution was stirred for 20 min, diluted in ethyl acetate (20 mL), washed with water (10 mL), dried over Na2SO4, and concentrated. The residue was purified on a silica gel column, eluting with a mixture of MeOH and dichloromethane (2% MeOH) to afford the product as a pale yellow liquid 35 (400 mg, 85%).

Workup

  1. customAfter the volatiles were evaporated
  2. dissolutionthe residue was dissolved in dry acetonitrile (10 mL)
  3. stirringThe solution was stirred for 20 min
  4. washwashed with water (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with a mixture of MeOH and dichloromethane (2% MeOH)

Sources & evidence

ORD record
ord-fae3eb8ae541482c8d63afc0aea17e82
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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