Benzyl isocyanate → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

HRID 583772Notes

Reaction equation

HRID 583772 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH2:19])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C(OCC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH:19][C:29]([NH:28][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:30])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 696934745-Methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

Product 1

HCID 101271274-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Methyl-4-amino-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester from Step 2 (0.15 g, 0.5 mmol) was dissolved in hot 1,4-dioxane (6-8 mL) under an inert atmosphere, stirred, and treated with benzyl isocyanate (0.07 g, 0.5 mmol). After 72 hours at room temperature, the mixture was diluted with diethyl ether (50 mL). After another hour the precipitate was filtered off, rinsed with ether, and dried to afford 0.14 g of 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester; mp 216-217° C.

Workup

  1. filtrationAfter another hour the precipitate was filtered off
  2. washrinsed with ether
  3. customdried

Sources & evidence

ORD record
ord-b9300e120ec7418781332c808fd9c5ac
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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