Triethylamine → HCID 13066645, compound

HRID 1606634Notes

Reaction equation

HRID 1606634 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N([CH2:18][CH3:19])CC)C.[C:20]([O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27])(=[O:22])[CH3:21]>O1CCCC1>[C:20]([O:23][C:19]1[CH:18]=[CH:31][CH:32]=[CH:24][C:25]=1[C:26]([NH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[O:23][C:20](=[O:22])[CH3:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:27])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 13066644Methyl 2,5-diaminobenzoate

Product 1

HCID 13066645HCID 13066645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3.32 g of methyl 2,5-diaminobenzoate, 5.8 ml of triethylamine and 20 ml of tetrahydrofuran was added dropwise to a solution of 8.7 g of 2-acetoxybenzoylchloride in 150 ml of tetrahydrofuran over 30 minutes, while stirring at 5° - 10°C. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour and then poured into 500 ml of ice-water to precipitate crystals. The crystals were recovered by filtration, washed with water and dried in air. Recrystallization from ethyl acetate gave 8.1 g of methyl 2,5-bis(2'-acetoxybenzamido)-benzoate having a melting point between 170° - 171°C.

Workup

  1. additionAfter completion of the addition
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. customto precipitate crystals
  4. filtrationThe crystals were recovered by filtration
  5. washwashed with water
  6. customdried in air
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f24dae2526d14aa3939cede6c2096675
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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