Acetic Acid → HCID 13785765, compound

HRID 1905623Notes

Reaction equation

HRID 1905623 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH3:15])=[CH:10][C:11]([O:13][CH3:14])=[O:12].[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.C(O)(=O)C.N1C2C=CC=CC=2N=CC(C(OC)=O)=C1>O1CCCC1.CC(C)=O>[CH3:15][C:9]1[NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][CH:20]([C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[C:17]([F:16])([F:26])[F:27])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 85903906HCID 85903906, compoundHCID 86741326HCID 86741326, compound

Product 1

HCID 13785765HCID 13785765, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(2-aminophenyl)amino]-2-butenoic acid, methyl ester (2.50 g., 12.0 mmole) in anhydrous tetrahydrofuran (12 ml.) is treated with 2-(trifluoromethyl)benzaldehyde (1.74 g., 10.0 mmole) and acetic acid (0.2 ml.). The resulting reaction mixture is stirred at room temperature under argon for 24 hours. The solvent is removed and the resulting yellow solid is triturated with isopropyl ether to give 3.27 g. of an off-white product. Recrystallization from dichloromethane-isopropyl ether gives 2.39 g. of 2,5-dihydro-4-methyl-2-2-(trifluoromethyl)phenyl]-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester; m.p. 190°-192°. TLC (silica gel; acetone:hexanes, 35:65) Rf =0.47.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent is removed
  3. customthe resulting yellow solid is triturated with isopropyl ether
  4. customto give 3.27 g
  5. customRecrystallization from dichloromethane-isopropyl ether
  6. customgives 2.39 g

Sources & evidence

ORD record
ord-8369ab3f38fc4a9e8954b1942a64417c
Source dataset
uspto-grants-1987_03
Patent number
US04647561

Reaction notes

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