Acetic Anhydride → HCID 20523567, compound

HRID 2059254Notes

Reaction equation

HRID 2059254 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18](O)=[O:19])=[O:15])=[C:6]1[CH3:25])[CH2:2][CH2:3][CH3:4].[CH3:26][N:27]([CH3:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH3:36])[CH3:35])[CH:29]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>O>[CH3:35][N:34]([CH3:36])[C:30]1[CH:29]=[C:28]([N:27]([CH3:37])[CH3:26])[CH:33]=[CH:32][C:31]=1[C:14]1([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]=2[CH3:25])[C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](=[O:19])[O:15]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 105559Benzoic acid, 2-[(1-butyl-2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 20523567HCID 20523567, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.35 g (0.01 mole) of 2-[(1-n-butyl-2-methyl-3-indolyl)carbonyl]benzoic acid, prepared as described in part A above, 1.80 g (0.011 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and five ml of acetic anhydride was stirred at ambient temperature for a period of approximately 18 hours. The reaction mixture was then poured into a mixture of 40 ml of water, 40 ml of ligroin and 20 ml of 10 percent aqueous sodium hydroxide. The ligroin layer was separated and the white crystals which separated from the solution on standing, were collected by filtration and dried to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1-n-butyl-2-methyl-3-indolyl)phthalide (Formula III: R°=R1 =R2 =R3 =Y1 =H; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =(CH2)3CH3) which melted at 165°-167° C. A characteristic infrared maximum appeared at 1752 cm-1 (C=O; s). A toluene solution of the product spotted on silica gel developed an intense purple-colored image.

Workup

  1. customprepared
  2. customThe ligroin layer was separated
  3. customthe white crystals which separated from the solution on standing
  4. filtrationwere collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-eb3e6ab39c414a3fb23f7bc0f4f16edb
Source dataset
uspto-grants-1982_03
Patent number
US04322352

Reaction notes

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