Benzyl isocyanate → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzyl ester

HRID 583767Notes

Reaction equation

HRID 583767 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([O:18][C:19]([C:21]1[S:22][C:23]([CH3:27])=[C:24]([NH2:26])[CH:25]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C(OCC)C>[CH2:11]([O:18][C:19]([C:21]1[S:22][C:23]([CH3:27])=[C:24]([NH:26][C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH:25]=1)=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 613104205-Methyl-4-amino-thiophene-2-carboxylic acid benzyl ester

Product 1

HCID 101504874-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzyl esterYield 65.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzyl isocyanate (0.29 g, 2.2 mmol) was added to a stirred solution of 5-methyl-4-amino-thiophene-2-carboxylic acid benzyl ester from Example 9, Step 2 (0.5 g, 2.0 mmol) in toluene (10-15 mL) at room temperature under an inert atmosphere. After 20 minutes, the mixture was heated to reflux for 10 minutes, allowed to cool, then diluted with an equal volume of diethyl ether. After 10 minutes, the precipitate was filtered off, rinsed with ether, and dried to afford 0.5 g of 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid benzyl ester; mp 208-209° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10 minutes
  3. temperatureto cool
  4. waitAfter 10 minutes
  5. filtrationthe precipitate was filtered off
  6. washrinsed with ether
  7. customdried

Sources & evidence

ORD record
ord-d877a4529ef941ea8f3f3d96ce885775
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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