Ethyl isocyanate → HCID 11741037, compound

HRID 1242629Notes

Reaction equation

HRID 1242629 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]=[C:8]2[C:16]([F:19])([F:18])[F:17].[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25]>C1COCC1>[CH2:24]([NH:26][C:27]([NH:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]=[C:8]2[C:16]([F:19])([F:17])[F:18])=[O:28])[CH3:25]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 21939647HCID 21939647, compound

Product 1

HCID 11741037HCID 11741037, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A stirred THF (5 mL) solution of 6-(2-aminobenzyl)-4-trifluoromethyl-1H-quinolin-2-one (Preparation #2, 50 mg, 157 μmol) was treated dropwise with a solution of EtNCO (78 μL, 985 μmol) in anhydrous THF (1 mL) at 0° C. The reaction mixture was allowed to warm to 20° C., before being stirred for 36 h. The precipitate formed was collected, washed with THF, & dried to give the title compound (38 mg, 62%): δH ((CD3)2SO)=1.00 (t, 3H), 3.05 (q, 2H), 4.00 (s, 2H), 6.30 (t, 1H), 6.90–6.95 (m, 2H), 7.05 (d, 1H), 7.15 (t, 1H), 7.35 (d, 1H), 7.40 (d, 1H), 7.55 (s, 1H), 7.70–7.80 (m, 2H); m/z (ES+)=390.2 [M+H]+.

Workup

  1. customThe precipitate formed
  2. customwas collected
  3. washwashed with THF
  4. customdried

Sources & evidence

ORD record
ord-22446ab2c92d4b79ba4a155aaf89d952
Source dataset
uspto-grants-2006_10
Patent number
US07115745B2

Reaction notes

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