4,4'-Dichlorobenzhydryl chloride → 4-[1-[3-[Bis(4-chlorophenyl)methylamino]benzoyl]indol-3-yl]butyric acid

HRID 1974570Notes

Reaction equation

HRID 1974570 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:8]1)=[O:6].C(N(C(C)C)CC)(C)C.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41](Cl)[C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=2)=[CH:37][CH:36]=1>C(Cl)(Cl)(Cl)Cl>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([CH:41]([NH:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:8]2)=[O:6])[C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=2)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 130784,4'-Dichlorobenzhydryl chlorideHCID 81531DiisopropylethylamineHCID 10618422HCID 10618422, compound

Product 1

HCID 191017624-[1-[3-[Bis(4-chlorophenyl)methylamino]benzoyl]indol-3-yl]butyric acidYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-[1-(3-aminobenzoyl)indol-3-yl]butyric acid (1.0 g) and diisopropylethylamine (1.3 g) in carbon tetrachloride (20 ml) was added bis(4-chlorophenyl)methyl chloride (0.84 g). The mixture was refluxed for 6 hours and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (20 ml) and diluted hydrochloric acid (30 ml) and washed with water (30 ml×3). The solution was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified by a column of silica gel to give a yellow solid of 4-[1-[3-[bis(4-chlorophenyl)methylamino]benzoyl]indol-3-yl]butyric acid (1.19 g).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  4. washdiluted hydrochloric acid (30 ml) and washed with water (30 ml×3)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by a column of silica gel

Sources & evidence

ORD record
ord-e6d45185a0f44770bcf28bd294885a58
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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