Triethylamine → HCID 20468635, compound

HRID 1903352Notes

Reaction equation

HRID 1903352 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].CNC([OH:29])C.[CH2:30]([N:32]([CH2:35]C)CC)[CH3:31]>C1COCC1>[OH:29][CH2:31][CH2:30][N:32]([CH3:35])[C:10](=[O:11])[C:9]1[CH:13]=[C:5]([O:4][C:3]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:2]=2[Cl:1])[CH:6]=[CH:7][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chlorideHCID 5247031N-Methylaminoethanol

Product 1

HCID 20468635HCID 20468635, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl chloride (7 g, 0.0184 mole) was added over 1 hr to a solution of N-methylaminoethanol (2.8 g, 0.0372 mole), triethylamine (3.7 g, 0.0368 mole) and THF (30 ml) at 25°-38°. The resulting mixture was heated to and held at reflux for 1.5 hrs., cooled and concentrated. The residue was taken into 400 ml of ether, washed three times with water, dried over MgSO4 and concentrated to 7.8 g of crude product. Kugelrohr distillation under reduced pressure afforded 3.0 g of pure N-(2-Hydroxyethyl)-N-methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide as a gum; nmr (CDCl3) δ 2.95-3.08 (2S, 3H); 3.22-3.82 (m) 4.74 (s, 1H), 7.04-8.52 (m, 6H); ir (CHCl3) 3640, 3420, 1648 Cm-1.

Workup

  1. temperatureThe resulting mixture was heated to and
  2. temperatureat reflux for 1.5 hrs
  3. temperature, cooled
  4. concentrationconcentrated
  5. washwashed three times with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to 7.8 g of crude product
  8. distillationKugelrohr distillation under reduced pressure

Sources & evidence

ORD record
ord-286be7e07d8f48a9bba9c35cad4dcd67
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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