Hydrochloric Acid → HCID 23282595, compound

HRID 369900Notes

Reaction equation

HRID 369900 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([CH2:18][CH2:19][C:20]([NH:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[O:21])[CH:15]=[CH:14][C:4]=1[C:5]([CH2:7]P(=O)(OC)OC)=[O:6].[C:32]([OH:36])(=[O:35])[CH:33]=O.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([CH2:18][CH2:19][C:20]([NH:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[O:21])[CH:15]=[CH:14][C:4]=1[C:5](=[O:6])/[CH:7]=[CH:33]/[C:32]([OH:36])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 14798Sodium HydroxideHCID 53661054HCID 53661054, compound

Product 1

HCID 23282595HCID 23282595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl [{2-methoxy-4-[2-(2-benzothiazolylaminocarbonyl)ethyl]benzoyl}methyl]phosphonate (6.4 g) in tetrahydrofuran (100 ml) is added 40% glyoxylic acid (7.7 ml), and further thereto is added dropwise a 5% aqueous sodium hydroxide solution (70 ml) under ice-cooling. The mixture is stirred for 30 minutes, and the mixture is acidified with 5% hydrochloric acid. The precipitated yellow powder is collected by filtration, washed with ethanol, dried, and then recrystallized from dimethylformamide-ethanol to give 2-{2-[3-methoxy-4-(trans-3-carboxyacryloyl)phenyl]ethylcarbonyl amino}benzothiazole (4.0 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated yellow powder is collected by filtration
  3. washwashed with ethanol
  4. customdried
  5. customrecrystallized from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-a28dad2c4dc24ba6a60d75f7f5792267
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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