Triethylamine → HCID 59919875, compound

HRID 342448Notes

Reaction equation

HRID 342448 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:20][C:21]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:23]2[C:24]([O:26][C:27](=O)[C:22]=12)=[O:25]>ClCCl>[Cl:20][C:21]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:23]2[C:24]([N:1]([C:2]3[C:7]4[O:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:6]=4[CH:5]=[CH:4][CH:3]=3)[C:27](=[O:26])[C:22]=12)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782183,6-Dichlorophthalic anhydrideHCID 22725354HCID 22725354, compound

Product 1

HCID 59919875HCID 59919875, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-amino-2,3-dimethylbenzo[b]furan (161 mg), triethylamine (202 mg) and 3,6-dichlorophthalic anhydride (261 mg) in dichloromethane (5 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was washed with 1N-hydrochloric acid and brine, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in methanol and treated with diazomethane. The separated solid was collected and washed with methanol to give 7-(3,6-dichlorophthalimido)-2,3-dimethylbenzo[b]furan (250 mg).

Workup

  1. washThe reaction mixture was washed with 1N-hydrochloric acid and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methanol
  5. additiontreated with diazomethane
  6. customThe separated solid was collected
  7. washwashed with methanol

Sources & evidence

ORD record
ord-e3e72c88d0ba412fb5f1891472c05201
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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