Hydrochloric Acid → HCID 11760869, compound

HRID 1598899Notes

Reaction equation

HRID 1598899 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[O:9])[CH:2]=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>CN(C)C=O.O>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:9])[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:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69303m-Tolyl isocyanateHCID 376124HCID 376124, compound

Product 1

HCID 11760869HCID 11760869, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of m-tolylisocyanate (0.846 g, 6.35 mmol) in dimethylformamide (3 ml) is added to a solution of the salt 3a prepared in Preparation 3 (1.937 g, 5.78 mmol) in dimethylformamide (8 ml). Triethylamine (32 ml) is added at 0° C. The mixture is stirred at 0° C. for 30 minutes and then at room temperature overnight. Water and then 10% hydrochloric acid are added. The mixture is extracted with ethyl acetate. The extract is washed with water and dried (sodium sulfate), and then the solvent is distilled off under reduced pressure. The residue is recrystallized from acetonitrile to obtain the objective compound 4a (1.39 g; yield 62%).

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. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0ed97942d3114ef5aa7c1bcf5d02b531
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

Loading…