Triethylamine → HCID 59815657, compound

HRID 2117355Notes

Reaction equation

HRID 2117355 reaction equation
CC1C=CC(S(O[C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:21])=[CH:14][N:13]=2)(=O)=O)=CC=1.[CH2:22]([O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([NH:34][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:21])=[CH:14][N:13]=2)=[CH:35][CH:36]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 228604-BenzyloxyanilineHCID 59815649HCID 59815649, compound

Product 1

HCID 59815657HCID 59815657, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

5-Bromo-3-nitropyridin-2-yl 4-methylbenzenesulfonate (38.2 g, 0.102 mmol) and 4-benzyloxyaniline (24.13 g, 0.102 mmol) were suspended in 900 mL of toluene under N2, treated with triethylamine (14.27 mL, 0.102 mmol) and the mixture heated at 110° C. for 16 h. Then, the reaction mixture was diluted with CH2Cl2 (1 L), washed with 2M HCl (aq) (4×500 mL) and brine (500 mL), and the combined organic extracts dried over Na2SO4 and then concentrated in vacuo. The crude product thus isolated was crystallized twice from ethanol to yield N-[4-(benzyloxy)phenyl]-5-bromo-3-nitropyridin-2-amine. 1H NMR (400 MHz, CDCl3) δ 5.11 (s, 2H), 7.04 (d, 2H, J=9.2 Hz), 7.34-7.50 (m, 7H), 8.48 (d, 1H, J=2.4 Hz), 8.66 (d, 1H, J=2.4 Hz), 9.94 (bs, 1H).

Workup

  1. washwashed with 2M HCl (aq) (4×500 mL) and brine (500 mL)
  2. dry with materialthe combined organic extracts dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product thus isolated
  5. customwas crystallized twice from ethanol

Sources & evidence

ORD record
ord-6b1d5b693a354a17a206b1cf117bbd7f
Source dataset
uspto-grants-2008_10
Patent number
US07442709B2

Reaction notes

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