Water → HCID 893019, compound

HRID 925027Notes

Reaction equation

HRID 925027 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].CCN([CH2:17][CH3:18])CC.Cl[CH2:20]Cl.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25]C=1.[OH2:29]>>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][C:20](=[O:29])[C:27]1[CH:26]=[CH:25][C:17]([CH3:18])=[CH:23][CH:28]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 962WaterHCID 6115AnilineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 805742-tert-Butylaniline

Product 1

HCID 893019HCID 893019, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

2-tert-butylaniline (14.0 mL, 90 mmol) and NEt3 (14.0 mL, 100 mmol) were added to 100 mL of dichloromethane and cooled to 0° C. P-toluoylchloride (12.0 mL, 90 mmol) was added dropwise to the cooled aniline solution, affording a suspension after complete addition. The slurry was warmed to room temperature and heated to reflux overnight. The suspension was taken to dryness and the solid was treated with 150 mL of water. The solid was collected by filtration, washed with 150 mL of diethylether and dried in vacuo, yielding 23.14 g (96%) of white solid. 1H NMR (400 MHz, CDCl3): 7.86 (s, 1H), 7.80 (d, 2H), 7.74 (d, 1H), 7.43 (d, 1H), 7.31 (d, 2H), 7.26 (d, 1H), 7.17 (t, 1H), 2.44 (s, 3H), 1.45 (s, 9H).

Workup

  1. customaffording a suspension
  2. additionafter complete addition
  3. temperatureThe slurry was warmed to room temperature
  4. temperatureheated
  5. temperatureto reflux overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with 150 mL of diethylether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c22593a6646f409e95e869ac6c101b69
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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