Triethylamine → HCID 15229769, compound

HRID 1609579Notes

Reaction equation

HRID 1609579 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][C:17](=[O:18])[NH:16][CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 665872-Dibenzofuranol

Product 1

HCID 15229769HCID 15229769, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-hydroxydibenzofuran (5.0 g, 27 mmol), methyl isocyanate (1.9 mL, 32 mmol) and triethylamine (3.0 mL, 22 mmol) in 75 mL of methylene chloride was stirred under nitrogen at room temperature overnight. During this time a solid formed. Additional methylene chloride was added and the solid dissolved. The reaction was then extracted with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 5.47 g of a yellow solid. Recrystallization from isopropyl ether gave 3.43 g (52%) of the title compound as a light brown crystalline solid, mp 155°-156° C.

Workup

  1. customDuring this time a solid formed
  2. dissolutionthe solid dissolved
  3. extractionThe reaction was then extracted with 1N HCl
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-982f34ea3a5a46da9a3a13003b72fef4
Source dataset
uspto-grants-1995_03
Patent number
US05401769

Reaction notes

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