2-Furancarboxylic acid → HCID 682134, compound

HRID 1835378Notes

Reaction equation

HRID 1835378 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][C:18]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][CH:11]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[S:17][C:18]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:14][CH:15]=1)=[O:8]

Participants

6

Reactant 4

HCID 69192-Furancarboxylic acidHCID 7087Dehydrothio-4-toluidineHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 682134HCID 682134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

First Route: 2-Furoic acid (1.85 gms, 16.5 mmole) was dissolved in anhydrous methylene chloride (30 mls), to which solution was added a suspension of 2-(4-amino-phenyl)-6-methyl benzothiazole (4.76 g., 16.5 mmole) and N-methyl morpholine (2.0 g., 16.5 mmole) in methylene chloride (30 mls, at room temperature). Then, 1-hydroxy-benzotriazole hydrate (2.67 g., 16.5 mmole) and 1-(3-dimethyl amino propyl)-3-ethyl carbodiimide hydrochloride (4.75 g., 16.5 mmole) were added at room temperature. More methylene chloride (20 ml.) was added with stirring at room temperature, and the reaction maintained overnight. The initial clear reaction solution changed to a turbid solution. More methylene chloride (10 ml.) was added to the product mixture, which was then extracted with 1N HCl to separate a solid. The solid was filtered and washed with water. The product solid was crystallized from large amount of MeOH to yield 2.19 gm. (33.1%). mp. 238-240° C. 1R and 13C NMR were consistent with the expected product. TLC showed one spot (5% MeOH—CH2Cl2 as developing solvent on silica gel plate).

Workup

  1. additionwas added
  2. temperaturethe reaction maintained overnight
  3. extractionwas then extracted with 1N HCl
  4. customto separate a solid
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customThe product solid was crystallized from large amount of MeOH
  8. customto yield 2.19 gm

Sources & evidence

ORD record
ord-ded71abd621040deb40692c153503b8e
Source dataset
uspto-grants-2004_08
Patent number
US06770663B2

Reaction notes

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