Hydrochloric Acid → HCID 18930594, compound

HRID 1598900Notes

Reaction equation

HRID 1598900 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.Br.[NH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20])=[O:15].C(N(CC)CC)C.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:10])[NH:12][CH2:13][C:14]([NH:16][C:17]2[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=2[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:20])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 376124HCID 376124, compound

Product 1

HCID 18930594HCID 18930594, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of m-chlorophenylisocyanate (756 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 (1.67 μl, 12 mmol) is added at 0 ° C., and the mixture is stirred at 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/diisopropylalcohol to obtain the objective compound 6u (1.43 g; yield 73%).

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/diisopropylalcohol

Sources & evidence

ORD record
ord-79514dc844c4459a9a874256f728cb47
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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