Benzylamine → N-Benzyl-3-hydroxythiophene-2-carboxamide

HRID 1445339Notes

Reaction equation

HRID 1445339 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C>[CH2:10]([NH:17][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[OH:1])=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 547155433-Hydroxythiophene-2-carboxylic acid

Product 1

HCID 54704139N-Benzyl-3-hydroxythiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

1.44 g of 3-hydroxy-thiophene-2-carboxylic acid were dissolved in 100 ml of dichloromethane, and 2.18 ml of benzylamine and 5.00 ml of a 50% strength 1-propanephosphoric anhydride solution in acetic acid were added. The reaction mixture was stirred at 22° C. for 2 h and, after addition of 100 ml of saturated sodium bicarbonate solution, extracted twice with 100 ml of dichloromethane each time. The combined organic phases were washed with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The product with the molecular weight of 233.3 (C12H11NO2S), MS (ESI): 234 (M+h+) was obtained.

Workup

  1. extractionextracted twice with 100 ml of dichloromethane each time
  2. washThe combined organic phases were washed with 100 ml of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 233.3 (C12H11NO2S), MS (ESI): 234 (M+h+) was obtained

Sources & evidence

ORD record
ord-3e2dc9052fd44cb1968b0c0906117366
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

Loading…