Triethylamine → HCID 22506607, compound

HRID 2233159Notes

Reaction equation

HRID 2233159 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.CCN(CC)CC>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:16]1[CH2:15][NH2:14])(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 195092-Pyridinemethanamine

Product 1

HCID 22506607HCID 22506607, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-nitrobenzenesulfonylchloride (16.62 g, 0.075 mol) in dry CH2Cl2 (120 mL) was added dropwise via cannula to a stirred solution of 2-(aminomethyl)pyridine (5.41 g, 0.05 mol) and Et3N (13.9 mL, 0.10 mol) in dry CH2Cl2 (150 mL) under nitrogen. The reaction mixture was stirred for three hours at room temperature, and then quenched with water (20 mL). The aqueous layer was separated and extracted with EtOAc (5×80 mL). The combined organic extracts were dried (MgSO4) and evaporated to small volume to give a white precipitate which was collected by filtration and washed with cold CH2Cl2 to give the desired product (11.37 g, 78%) as a white solid: 1H NMR (Acetone-d6) δ 4.46 (s, 2H), 7.19 (dd, 1H, J=7.4, 4.5 Hz), 7.25-7.35 (br s, 1H), 7.39 (d, 1H, J=7.7 Hz), 7.68 (ddd, 1H, J=7.7, 7.5, 1.8 Hz), 7.76-7.88 (m, 2H), 7.94 (dd, 1H, J=7.7, 1.5 Hz), 8.04 (dd, 1H, J=7.5, 1.8 Hz), 8.38 (d, 1H, J=4.5 Hz).

Workup

  1. customquenched with water (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (5×80 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated to small volume
  6. customto give a white precipitate which
  7. filtrationwas collected by filtration
  8. washwashed with cold CH2Cl2

Sources & evidence

ORD record
ord-1ec09f2f590b4637840393993b3e8ba9
Source dataset
uspto-grants-2010_05
Patent number
US07709486B2

Reaction notes

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