Water → HCID 178507374, compound

HRID 441659Notes

Reaction equation

HRID 441659 reaction equation
[NH:1]1[C:5]([NH:6][C:7]([C:9]2[C:17](=[O:18])[N:16]3[C:12]([S:13][C:14]4[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:15]=43)=[N:11][CH:10]=2)=[O:8])=[N:4][N:3]=[N:2]1.O.[OH-].[Na+].[H][H]>[Pt]=O.CN(C)C=O>[NH:1]1[C:5]([NH:6][C:7]([C:9]2[C:17](=[O:18])[N:16]3[C:12]([S:13][C:14]4[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:15]=43)=[N:11][CH:10]=2)=[O:8])=[N:4][N:3]=[N:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compoundHCID 178522709HCID 178522709, compound

Product 1

HCID 178507374HCID 178507374, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4.5 g. of N-(5-tetrazolyl)-7-nitro-4-oxo-4H-pyrimido[2,1-b]benzothiazole-3-carboxamide in 50 ml. of water and 25 ml. of dimethylformamide is added sufficient 1N aqueous sodium hydroxide to effect a solution. Platinum oxide (300 mg.) is added and the suspension shaken in a hydrogen atmosphere at an initial pressure of 30 p.s.i. When the theoretical amount of hydrogen is absorbed the spent catalyst is filtered and the filtrate treated with sufficient 6N hydrochloric acid to register acid to Congo red paper. The acidified filtrate is further diluted with 25 ml. of water and cooled in an ice bath. The desired product is filtered and recrystallized from dimethylformamide.

Workup

  1. additionTo a suspension of 4.5 g
  2. customWhen the theoretical amount of hydrogen is absorbed the spent catalyst
  3. filtrationis filtered
  4. additionthe filtrate treated with sufficient 6N hydrochloric acid
  5. additionThe acidified filtrate is further diluted with 25 ml
  6. temperatureof water and cooled in an ice bath
  7. filtrationThe desired product is filtered
  8. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-b26d03d5b66f49f0942513e59ff6b563
Source dataset
uspto-grants-1977_08
Patent number
US04041163

Reaction notes

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