Sodium Hydroxide → N-[6-(n-butyl)-4H-1-benzothiopyran-4-on-3-yl)-oxalic acid monoamide

HRID 65468Notes

Reaction equation

HRID 65468 reaction equation
C[N:2]([C:8]1[C:13](=[O:14])[C:12]2[CH:15]=[C:16]([CH2:19][CH2:20][CH2:21][CH3:22])[CH:17]=[CH:18][C:11]=2[S:10][CH:9]=1)[C:3]([C:5](N)=[O:6])=[O:4].[OH-:23].[Na+]>C(O)C.O>[CH2:19]([C:16]1[CH:17]=[CH:18][C:11]2[S:10][CH:9]=[C:8]([NH:2][C:3](=[O:4])[C:5]([OH:6])=[O:23])[C:13](=[O:14])[C:12]=2[CH:15]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86741043N-[6-(n-butyl)-4H-1-benzothiopyran-4-on-3-yl]-oxamide methyl ester

Product 1

HCID 54266020N-[6-(n-butyl)-4H-1-benzothiopyran-4-on-3-yl)-oxalic acid monoamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6.15 g (0.0193 mol) of N-[6-(n-butyl)-4H-1-benzothiopyran-4-on-3-yl]-oxamide methyl ester are stirred with a solution of 22.6 ml of 1N sodium hydroxide solution in 147 ml of ethanol and 970 ml of water for 2 hours at 70°. A small degree of cloudiness is then removed by filtration and the filtrate is acidified with hydrochloric acid, a crystalline product being precipitated. After cooling, the crystals are filtered with suction and washed first with water, then with ethanol and subsequently with ether. After drying there is obtained N-[6-(n-butyl)-4H-1-benzothiopyran-4-on-3-yl)-oxalic acid monoamide having a melting point of 208° (decomposition).

Workup

  1. customA small degree of cloudiness is then removed by filtration
  2. customa crystalline product being precipitated
  3. temperatureAfter cooling
  4. filtrationthe crystals are filtered with suction
  5. washwashed first with water
  6. customAfter drying there

Sources & evidence

ORD record
ord-033a7a6fcafa43958510dc1973ea2fb3
Source dataset
uspto-grants-1986_09
Patent number
US04614745

Reaction notes

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