Triethylamine → HCID 11404888, compound

HRID 1857480Notes

Reaction equation

HRID 1857480 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[CH:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](OC2C=CC=CC=2)=[N:22][C:23]#[N:24])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[C:23]([NH:22][C:21](=[N:6][C:5]1[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=1)[O:20][C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6056715-(Trifluoromethyl)-m-anisidineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 11404888HCID 11404888, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyloxy-5-trifluoromethylaniline (11 mmol, 2.10 g) in dichloromethane (25 ml), diphenylcyanocarbonimidate (10 mmol, 2.38 g) and triethylamine (11 mmol, 1.53 ml) were added. The reaction mixture was stirred under nitrogen for 16 h at room temperature. After concentration the residue was stirred with water, the water was decanted followed by concentration. The residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give 0.413 g of the title compound (12%); Mp 168.5-169.5° C.; 1H-NMR (CDCl3): δ 3.83 (s, 3H), 7.00 (s, 1H), 7.14 (m, 3H), 7,23 (s, 1H), 7.32 (t, 1H), 7.43 ppm (t, 2H), 8.7 (br s, 1H). EI SP/MS: 335 (M+).

Workup

  1. concentrationAfter concentration the residue
  2. stirringwas stirred with water
  3. customthe water was decanted
  4. concentrationfollowed by concentration
  5. customThe residue was purified by flash chromatography (ethyl acetate/heptane 1:2)

Sources & evidence

ORD record
ord-ca26e8c4e0bf4756899e8dfaa4d04b4f
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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