Triethylamine → HCID 59815657, compound

HRID 499046Notes

Reaction equation

HRID 499046 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-feaa98f873ec48e3815ebccfcec07d8e
Source dataset
uspto-grants-2010_08
Patent number
US07767673B2

Reaction notes

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