Triethylamine → HCID 15537968, compound

HRID 1836924Notes

Reaction equation

HRID 1836924 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[S:3]1.C(N(CC)CC)C.C(Cl)(=O)OCC.[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1)([O-:35])=[O:34]>C(Cl)Cl>[N+:33]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][NH:41][C:14](=[O:16])[C:13]2[CH:17]=[C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])[CH:10]=[CH:11][C:12]=2[O:18][CH3:19])=[CH:42][CH:43]=1)([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 291474-NitrobenzylamineHCID 9943613HCID 9943613, compound

Product 1

HCID 15537968HCID 15537968, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid (422 mg, 1.50 mmol), triethylamine (0.732 mL, 5.25 mmol) and methylene chloride (7 mL) were mixed and ethyl chlorocarbonate (0.158 mL, 1.50 mmol) was added under cooling with ice and stirring. After stirring for 10 minutes under cooling with ice, 4-nitrobenzylamine (283 mg, 1.50 mmol) was added. The mixture was stirred for 2 hours at room temperature, and then allowed to stand overnight. After washed with water, the reaction mixture was dried over anhydrous sodium sulfate and concentrated. The residue was dissolved into water (20 mL), which was made acidic with 10% hydrochloric acid and stirred for 2 hours. The precipitated crystals were collected by filtration, washed with water and dried, then they were recrystallized from ethanol to obtain 472 mg (75%) of the title compound as pale yellow prisms.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring for 10 minutes
  3. additionwas added
  4. stirringThe mixture was stirred for 2 hours at room temperature
  5. washAfter washed with water
  6. dry with materialthe reaction mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved into water (20 mL), which
  9. stirringstirred for 2 hours
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with water
  12. customdried
  13. customthey were recrystallized from ethanol

Sources & evidence

ORD record
ord-be7dd842e84346eb98926c17b8bc24d6
Source dataset
uspto-grants-2004_08
Patent number
US06780431B1

Reaction notes

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