Methanol → HCID 178431699, compound

HRID 733636Notes

Reaction equation

HRID 733636 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:20]=[CH:21][C:22]2[C:27](=[O:28])[O:26][C:25]([CH3:30])([CH3:29])[O:24][C:23]=2[CH:31]=1.O.CO>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:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26][C:25]([CH3:29])([CH3:30])[O:24][C:23]=4[CH:31]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 112534834-[(4-Chlorophenyl)ethynyl]benzaldehydeHCID 231100727-Amino-2,2-dimethyl-4H-1,3-benzodioxine-4-one

Product 1

HCID 178431699HCID 178431699, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-[(4-chlorophenyl)ethynyl]benzaldehyde (1.31 g, 5.43 mmol) and 7-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one (1.00 g, 5.18 mmol) in toluene (20 ml) was heated at reflux for 18 h with azeotropic removal of water. Then the reaction mixture was cooled to rt and MeOH (20 ml) was added. The precipitate was filtered off, washed with MeOH and dried under reduced pressure to give 1.95 g of the titled compound as a yellow powder (91%). 1H NMR (CDCl3, 300 MHz) δ 8.42 (s, 1H), 7.99 (d, J=8.3 Hz, 1H), 7.91 (d, J=8.2 Hz, 2H, 7.65 (d, J=8.2 Hz, 2H), 7.50 (d, J=8.7 Hz, 2H), 7.37 (d, J=8.7 Hz, 2H), 6.91 (dd, J=8.3, 1.9 Hz, 1H), 6.74 (d, J=1.9 Hz, 1H), 1.77 (s, 6H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with MeOH
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-4f1a5d3122544e67992d580b6947d8d0
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

Loading…