Acetic Anhydride → HCID 20523545, compound

HRID 1413870Notes

Reaction equation

HRID 1413870 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=O)=[O:13])=[C:4]1[CH3:23])[CH3:2].[CH2:24]([N:26]([CH2:38][CH3:39])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH:28]=1)[CH3:25].C(OC(=O)C)(=O)C>C(O)C>[CH2:34]([N:33]([CH2:36][CH3:37])[C:29]1[CH:28]=[C:27]([N:26]([CH2:24][CH3:25])[CH2:38][CH3:39])[CH:32]=[CH:31][C:30]=1[C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH3:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:18])[O:13]1)[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-HCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamine

Product 1

HCID 20523545HCID 20523545, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.28 g (0.04 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]benzoic acid, prepared as described in part A above, 10.7 g (0.043 mole) of 90 percent active N,N,N',N'-tetraethyl-m-phenylenediamine and 6.0 ml of acetic anhydride was stirred at room temperature for seventeen hours. The reaction mixture was diluted with 26.0 ml of ethanol, stirred and filtered. The separated solid was washed with diethylether and dried to yield 11.8 g of 3-[2,4-bis(diethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =Y1 =H; R=R6 =CH2CH3 ; R4 =N(CH2CH3)2 ; R5 =CH3), a white crystalline material which melted at 139°-140° C. The infrared spectrum showed a significant band at 1760 cm-1 (C=O; s) and the nuclear magnetic resonance spectrum was in accord with the structure. A solution of this product in benzene developed a deep blue-black color when spotted on silica gel.

Workup

  1. customprepared
  2. stirringstirred
  3. filtrationfiltered
  4. washThe separated solid was washed with diethylether
  5. customdried

Sources & evidence

ORD record
ord-1b4cb5d1d9a945c68d0c84254255defc
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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