Water → HCID 69202399, compound

HRID 1392945Notes

Reaction equation

HRID 1392945 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)(=[O:26])=[O:27])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Product 1

HCID 69202399HCID 69202399, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 4-nitro benzenesulfonyl chloride (292 mg, 1.320 mmol) and triethylamine (220 mg, 2.169 mmol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 4 h. Water (10 mL) followed by dichloromethane (10 mL) were added to the reaction mixture and the organic layer was separated, dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 12g as a solid (120 mg, 33.3%). HPLC: 97% (Rt=7.76 min).

Workup

  1. additionwere added to the reaction mixture
  2. customthe organic layer was separated
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1d836103dca04f9b8e13204af5a2e963
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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