Water → HCID 178431704, compound

HRID 551944

Reaction equation

HRID 551944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:31]=[CH:30][C:22]2[O:23][C:24]([CH3:29])([CH3:28])[O:25][C:26](=[O:27])[C:21]=2[CH:20]=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13](/[CH:14]=[N:18]/[C:19]3[CH:31]=[CH:30][C:22]4[O:23][C:24]([CH3:28])([CH3:29])[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 112534834-[(4-Chlorophenyl)ethynyl]benzaldehydeHCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 178431704HCID 178431704, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-[(4-chlorophenyl)ethynyl]benzaldehyde (2.60 g, 10.9 mmol, intermediate which may be prepared according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one (2.00 g, 10.36 mmol) in toluene (40 mL) was heated at reflux for 2 hrs with azeotropic removal of water. Then the temperature was cooled down slowly. A yellow solid precipitated out and MeOH (40 mL) was added. The precipitate was filtered, washed with MeOH (2×) and dried under reduced pressure to give 3.98 g (92%) of the title compound as a yellow powder. 1H NMR (CDCl3) δ: 8.53 (s, 1H), 7.90 (d, J=8.2 Hz, 2H), 7.85 (d, J=2.5 Hz, 1H), 7.64 (d, J=8.2 Hz, 2H), 7.53 (dd, J=8.6, 2.5 Hz, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H), 7.03 (d, J=8.6 Hz, 1H).

Workup

  1. temperatureThen the temperature was cooled down slowly
  2. customA yellow solid precipitated out and MeOH (40 mL)
  3. additionwas added
  4. filtrationThe precipitate was filtered
  5. washwashed with MeOH (2×)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e56071e3d0b14935a3fcff0403fc33fb
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Linked notes

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