2-Benzofurancarboxaldehyde → HCID 9927809, compound

HRID 602513Notes

Reaction equation

HRID 602513 reaction equation
[CH2:1]([O:4][C:5](=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:14])[CH2:2][CH3:3].[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[CH:25]=O>O1CCCC1>[CH2:1]([O:4][C:5](=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:25][C:17]2[O:16][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH:18]=2)=[CH:9][C:8]=1[CH3:14])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 613412-BenzofurancarboxaldehydeHCID 56953891HCID 56953891, compound

Product 1

HCID 9927809HCID 9927809, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.1 M solution of (4-amino-2-methylphenyl)-carbamic acid propyl ester (0.35 mL, 0.035 mmol) and 0.1 M solution of benzofuran-2-carbaldehyde (0.35 mL) in tetrahydrofuran (THF) was kept at 55° C. for 60 minutes. Volatiles were removed in vacuo. To the obtained residue 0.2 M sodium cyanoborohydride (NaBH3CN) (0.5 mL) in methanol and acetic acid (0.03 mL) were added. After sonication for 60 minutes the reaction mixture was evaporated in vacuo and the title compound was separated by preparative LC/MS to give 5.1 mg of colorless solid. Yield 43%. LC/MS (m/z) 339.2 ([M+H]+); RT=2.92, (UV, ELSD) 94%, 94%.

Workup

  1. customVolatiles were removed in vacuo
  2. additionTo the obtained residue 0.2 M sodium cyanoborohydride (NaBH3CN) (0.5 mL) in methanol and acetic acid (0.03 mL) were added
  3. customAfter sonication for 60 minutes the reaction mixture
  4. customwas evaporated in vacuo
  5. customthe title compound was separated by preparative LC/MS

Sources & evidence

ORD record
ord-ba831cc8c27847a09f75aa65bcf1ffd4
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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