Hydrochloric Acid → HCID 13066646, compound

HRID 1606637Notes

Reaction equation

HRID 1606637 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([NH2:12])[CH:9]=[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].Cl>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]=[C:10]([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:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:27])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 12399493Methyl 2,4-diaminobenzoate

Product 1

HCID 13066646HCID 13066646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 6.64 g of methyl 2,4-diaminobenzoate, 11.5 ml of triethylamine and 50 ml of tetrahydrofuran was added dropwise to a solution of 17.4 g of 2-acetoxybenzoylchloride in 300 ml of tetrahydrofuran over 0.5 - 1 hour, while stirring at 5° - 10°C. The stirring was then continued at room temperature for 2 hours. The resulting reaction mixture was poured into 1.5 l of diluted hydrochloric acid to precipitate crystals. The crystals were recovered by filtration, washed with water, dried and recrystallized from ethyl acetate to yield 15 g of methyl 2,4-bis(2'-acetoxybenzamido)-benzoate having a melting point between 143° - 145°C.

Workup

  1. customThe resulting reaction mixture
  2. customto precipitate crystals
  3. filtrationThe crystals were recovered by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-41a7f1aefa4e4355a40e174210165ba3
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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