Hydrochloric Acid → HCID 68864584, compound

HRID 1725875Notes

Reaction equation

HRID 1725875 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[Si](C)(C)[CH3:16].[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl.N1C=CC=CC=1>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:1][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:3]([CH:7]=1)[C:4]([O:6][CH3:16])=[O:5])([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7369Benzenesulfonyl chlorideHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 68864584HCID 68864584, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-5-nitrobenzoic acid (151 mg, 0.77 mmol) in dichloromethane (2.0 mL) was treated with chlorotrimethylsilane (1.70 mL of 1M solution in CH2Cl2, 1.70 mmol) and pyridine (2.0 mL), stirred at room temperature for 30 minutes, treated with benzenesulfonyl chloride (150 μL, 1.16 mmol), stirred overnight at room temperature, warmed to 40° C., stirred overnight, treated with 1N HCl (2.0 mL), and extracted with dichloromethane (2×). The combined extracts were washed with distilled water and brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(−)) m/e 335 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.96 (s, 1H), 8.58 (d, 1H), 8.39 (dd, 1H), 7.96 (m, 2H), 7.74-7.60 (m, 4H), 3.91 (s, 3H).

Workup

  1. stirringstirred overnight at room temperature
  2. temperaturewarmed to 40° C.
  3. stirringstirred overnight
  4. extractionextracted with dichloromethane (2×)
  5. washThe combined extracts were washed with distilled water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-98177669cfd7492a867ca12b375ad6b2
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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