Hydrochloric Acid → HCID 18930565, compound

HRID 1598903Notes

Reaction equation

HRID 1598903 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.Br.[NH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21])=[O:16].C(N(CC)CC)C.Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:11])[NH:13][CH2:14][C:15]([NH:17][C:18]2[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=2[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:21])=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 878433-Methoxyphenyl isocyanateHCID 376124HCID 376124, compound

Product 1

HCID 18930565HCID 18930565, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of m-methoxyphenylisocyanate (734 mg, 4.92 mmol) in tetrahydrofuran (8 ml) is added to a solution of the salt 3a (1.341 g, 4 mmol) prepared in Preparation 3 in tetrahydrofuran (50 ml). Triethylamine (558 μl, 4 mmol) is added at 0° C., and the mixture is stirred at 0°0 C. for 30 minutes and then at room temperature overnight. Water and then 10% hydrochloric acid are added, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried (sodium sulfate), and distilled under reduced pressure to remove the solvent. The residue is recrystallized from dichloromethane/diisopropylether to obtain the objective compound 6x (1.29 g, 80%).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried (sodium sulfate)
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue is recrystallized from dichloromethane/diisopropylether

Sources & evidence

ORD record
ord-917ea69b1d074c259b973ec260022639
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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