Hydrochloric Acid → 3-(3-Benzylureido)thiophene-2-carboxylic acid

HRID 576872Notes

Reaction equation

HRID 576872 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+].[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([NH:26][C:27](=[O:28])[NH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 76639Benzyl isocyanateHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 533974903-(3-Benzylureido)thiophene-2-carboxylic acidYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of methyl 3-amino-thiophene-2-carboxylate 9.43 g (60 mmol) in acetonitrile 12 ml, 2N-sodium hydroxide 36 ml (72 mmol) was added and the mixture was stirred for 5 hrs. at 85° C. The reaction mixture was neutralized with 2N-hydrochloric acid 36 ml (72 mmol), then saturated sodium bicarbonate solution 50 ml and a solution of benzyl isocyanate 7.41 ml (60 mmol) in acetonitrile 36 ml were added and the mixture was stirred overnight. The reaction mixture was basified with 2N-sodium hydroxide 60 ml and washed with ether 100 ml. The aqueous phase was acidified with 2N-hydrochloric acid 85 ml. The aqueous phase was filtered and washed with H2O. The solid was dried in vacuo to obtain the title compound 6.46 g (yield 39%)

Workup

  1. customat 85° C
  2. stirringthe mixture was stirred overnight
  3. washwashed with ether 100 ml
  4. filtrationThe aqueous phase was filtered
  5. washwashed with H2O
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-1b9a9d3ea51d451991bfe0a067186dd9
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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