Triethylamine → HCID 21884460, compound

HRID 722492Notes

Reaction equation

HRID 722492 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH2:23])[CH:17]=1.C(N(CC)CC)C>C1COCC1>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][C:18]=1[NH:23][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3518402-Amino-4-BromophenolHCID 123754634-Methoxy-3-nitrobenzoyl chloride

Product 1

HCID 21884460HCID 21884460, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-methoxy-3-nitro-benzoyl chloride (7.12 g, 33.0 mmol) in THF (50 ml) was added dropwise with stirring to a solution of 4-bromo-2-aminophenol (6.20 g, 33.0 mmol) in THF (50 ml) containing triethylamine (6.82 ml, 66.0 mmol). After addition was complete the reaction was stirred at room temperature overnight. The reaction mixture was concentrated to approximately half the original volume and the precipitate collected by filtration. The solid was washed with methanol and ether and dried under vacuum to give the subtitle compound as a brown solid (5.24 g, 42%). 1H NMR (DMSO) δ 8.58(d, 1H), 8.36(dd, 1H), 7.55(d, 1H), 6.96(m, 2H), 6.68(dd, 1H), 4.05(s, 3H).

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated to approximately half the original volume
  3. filtrationthe precipitate collected by filtration
  4. washThe solid was washed with methanol and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-56e172ca16ef445890f1efcdc0a25a01
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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