Acetic Acid → HCID 53706299, compound

HRID 369897Notes

Reaction equation

HRID 369897 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]([NH:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)=[O:21])[C:6]([CH2:8]P(=O)(OC)OC)=[O:7].[N:32]1[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=1.[OH-].[Na+].C(O)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH:8]=[CH:38][C:35]2[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]([NH:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 86755973HCID 86755973, compound

Product 1

HCID 53706299HCID 53706299, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl {[3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)benzoyl]methyl}phosphonate (1.7 g) and pyridine-4-aldehyde (0.5 g) in tetrahydrofuran (30 ml) is added a 5% aqueous sodium hydroxide solution (6 ml) under ice-cooling, and the mixture is stirred for 5 hours. The mixture is neutralized with acetic acid, and the precipitated crystals are collected by filtration, and then recrystallized from dichloromethane-ethanol-diethyl ether to give 2-{2-methoxy-4-[3-(4-pyridyl)acryloyl]phenoxymethylcarbonylamino}benzothiazole (1.3 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals are collected by filtration
  3. customrecrystallized from dichloromethane-ethanol-diethyl ether

Sources & evidence

ORD record
ord-6d8e43a0c2ed41cebd04923adf77c721
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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