2,6-Dichlorobenzaldehyde → HCID 13785763, compound

HRID 1905624Notes

Reaction equation

HRID 1905624 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].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=O>O1CCCC1.C(O)(=O)C.C(OC(C)C)(C)C>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]1[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([CH3:15])=[C:10]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 2

HCID 67372,6-DichlorobenzaldehydeHCID 85903906HCID 85903906, compound

Product 1

HCID 13785763HCID 13785763, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(2-aminophenyl)amino]-2-butenoic acid, methyl ester (4.74 g., 230 mmole) in anhydrous tetrahydrofuran (20 ml.) and acetic acid (0.2 ml.) is treated with 2,6-dichlorobenzaldehyde (4.03 g., 23.0 mmole). The resulting reaction mixture is stirred at room temperature for 4 days. The solvent is stripped off to give a brown oil which is dissolved in isopropyl ether and allowed to stand at 0°-5° (refrigerator) for 24 hours. The solid that precipitates is filtered off and washed with additional isopropyl ether. This product is triturated with isopropyl ether and filtered off to give 2-(2,6-dichlorophenyl)-2,5-dihydro-4-methyl-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester; 119°-120° (with decomposition). TLC (silica gel; ethyl acetate:hexanes, 40:60) Rf =0.38.

Workup

  1. customThe resulting reaction mixture
  2. customto give a brown oil which
  3. customto stand at 0°-5°
  4. customfor 24 hours
  5. customThe solid that precipitates
  6. filtrationis filtered off
  7. washwashed with additional isopropyl ether
  8. customThis product is triturated with isopropyl ether
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-c0d78c27a94e4ca9902ae14fb07d3ccd
Source dataset
uspto-grants-1987_03
Patent number
US04647561

Reaction notes

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