4-Toluenesulfonyl chloride → HCID 68982248, compound

HRID 1822177Notes

Reaction equation

HRID 1822177 reaction equation
[CH2:1]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=1)[CH:9]([CH3:12])[CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S([Cl:38])(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl>[CH2:1]([N:8]([CH:9]([CH3:12])[CH2:10][Cl:38])[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 8471TriethylamineHCID 3761652HCID 3761652, compound

Product 1

HCID 68982248HCID 68982248, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[benzyl(3-chloro-4-fluorophenyl)amino]propan-1-ol (1-6, 0.060 g, 0.204 mmol) in CH2Cl2 was treated with triethylamine (0.028 mL, 0.204 mmol) and TsCl (0.042 g, 0.204 mmol). The resulting solution was allowed to stir 12 h. Additional TsCl (0.084 g, 0.408 mmol) was added and allowed to stir until complete. Upon completion, the reaction mixture was partitioned between NaHCO3 (sat. aq) and CH2Cl2 (3×2 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated to yield N-benzyl-3-chloro-N-(2-chloro-1-methylethyl)-4-fluoroaniline.

Workup

  1. stirringto stir until complete
  2. customUpon completion, the reaction mixture was partitioned between NaHCO3 (sat. aq) and CH2Cl2 (3×2 mL)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42c6e5087e7a439ebb0e3732ac347dfe
Source dataset
uspto-grants-2009_10
Patent number
US07608739B2

Reaction notes

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