N,N-Dimethylbenzamide → 2-Thiophenecarboxylic acid

HRID 750437Notes

Reaction equation

HRID 750437 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]#[N:15].C(#N)C.[OH2:19].CN(C)[C:22](=[O:29])[C:23]1C=C[CH:26]=[CH:25][CH:24]=1>C(#N)C>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH2:15])=[O:29].[S:9]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:22]([OH:29])=[O:19]

Participants

7

Reactant 4

HCID 11916N,N-DimethylbenzamideHCID 62657Potassium Phosphate, TribasicHCID 660872-Thiophenecarbonitrile3×HCID 18373917Acetonitrile--water (1/1)

Product 2

HCID 107002-Thiophenecarboxylic acidHCID 220632-Thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 15-mL polypropylene centrifuge tube was added 3.86 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 0.1691 g of 2-thiophenecarbonitrile. The final concentration of 2-thiophencarbonitrile was 0.307 M. The reaction mixture was mixed on a rotating platform at 27° C. After 30 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 2-thiophenecarbonitrile was 99.5%, and the yields of 2-thiophenecarboxamide and 2-thiophenecarboxylic acid were 98% 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 27° C

Sources & evidence

ORD record
ord-bcf9deda78ac4f65afa391c60b6674e3
Source dataset
uspto-grants-2008_07
Patent number
US07405064B2

Reaction notes

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