Triethylamine → HCID 12848785, compound

HRID 1388364Notes

Reaction equation

HRID 1388364 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:4]=1[C:5](Cl)=[O:6].C(N(CC)CC)C.[CH2:23]([NH2:29])[CH:24]1[O:28][CH2:27][CH2:26][CH2:25]1>C(Cl)Cl.O.C1C=CC=CC=1>[CH2:23]([NH:29][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]([CH3:12])=[CH:11][C:3]=1[O:2][CH3:1])[CH:24]1[O:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 253298TetrahydrofurfurylamineHCID 20470960HCID 20470960, compound

Product 1

HCID 12848785HCID 12848785, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methoxy-4-methyl-5-nitrobenzoyl chloride (7.0 g), methylene chloride (35 ml) and triethylamine (7.68 g) is added a mixture of tetrahydrofurfurylamine (4.33 g) and dry benzene (11 ml) with ice cooling and stirring. The resultant mixture is allowed to stand at room temperature for 20 minutes, mixed with water and shaken with methylene chloride. The organic layer is dried over sodium sulfate and evaporated to remove the solvent. The residue is washed with ethyl acetate/isopropyl ether and recrystallized from methylene chloride/ethyl acetate to give N-tetrahydrofurfuryl-2-methoxy-4-methyl-5-nitrobenzamide (7.1 g) as crystals melting at 178° to 179.5° C.

Workup

  1. dry with materialThe organic layer is dried over sodium sulfate
  2. customevaporated
  3. customto remove the solvent
  4. washThe residue is washed with ethyl acetate/isopropyl ether
  5. customrecrystallized from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-89023ab14ef944efadde4c9aa3ea046a
Source dataset
uspto-grants-1984_02
Patent number
US04431663

Reaction notes

Loading…