N,N-Dimethylbenzamide → Pyrazinamide

HRID 1592799Notes

Reaction equation

HRID 1592799 reaction equation
P([O-])([O-])([O-])=[O:2].[K+].[K+].[K+].[N:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]#[N:16].C(#N)C.[OH2:20].CN(C)C(=[O:30])C1C=CC=CC=1>C(#N)C>[N:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([NH2:16])=[O:30].[N:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([OH:2])=[O:20]

Participants

7

Reactant 4

HCID 11916N,N-DimethylbenzamideHCID 62657Potassium Phosphate, TribasicHCID 73172Pyrazinecarbonitrile3×HCID 18373917Acetonitrile--water (1/1)

Product 2

HCID 1046PyrazinamideHCID 10472-Pyrazinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 15-mL polypropylene centrifuge tube was added 3.73 mL of 50 mM potassium phosphate buffer (pH 7.0), 1.0 mL of a suspension of 22.1 mg dry cell weight E. coli SW132 wet cells (prepared as described in Example 10) in 50 mM potassium phosphate buffer (pH 7.0), and 0.2694 g of pyrazinecarbonitrile. The final concentration of pyrazinecarbonitrile was 0.512 M. The reaction mixture was mixed on a rotating platform at 23° C. After 15 min, 7.50 mL of 95:5 acetonitrile/water containing 0.30 M N,N-dimethylbenzamide (HPLC external standard) was added to the reaction, the resulting mixture centrifuged, and a 0.100 mL of the supernatant mixed with 0.900 mL of acetonitrile and analyzed by HPLC. The conversion of pyrazinecarbonitrile was 100%, and the yields of pyrazinamide and pyrazinecarboxylic acid were 100% and 0%, respectively.

Workup

  1. customdry cell weight E
  2. customwet cells (prepared as described in Example 10) in 50 mM potassium phosphate buffer (pH 7.0)
  3. additionThe reaction mixture was mixed on a rotating platform at 23° C

Sources & evidence

ORD record
ord-d03c1eb31eb24f09b70c82db5eda5991
Source dataset
uspto-grants-2007_11
Patent number
US07294493B2

Reaction notes

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