Acetic Anhydride → HCID 20523539, compound

HRID 1413884Notes

Reaction equation

HRID 1413884 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[C:24]([Cl:25])=[C:23]([Cl:26])[C:22]([Cl:27])=[C:21]([Cl:28])[C:17]=2[C:18]([OH:20])=O)=[O:15])=[C:6]1[CH3:29])[CH2:2][CH2:3][CH3:4].[CH3:30][N:31]([CH3:41])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N:38]([CH3:40])[CH3:39])[CH:33]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>>[CH3:39][N:38]([CH3:40])[C:34]1[CH:33]=[C:32]([N:31]([CH3:41])[CH3:30])[CH:37]=[CH:36][C:35]=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[CH3:29])[C:16]2[C:17](=[C:21]([Cl:28])[C:22]([Cl:27])=[C:23]([Cl:26])[C:24]=2[Cl:25])[C:18](=[O:20])[O:15]1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 53975483HCID 53975483, compound

Product 1

HCID 20523539HCID 20523539, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 5.20 g (0.01 mole) of 2-[(1-n-butyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared in part A above, 2.0 g (0.012 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and five ml of acetic anhydride was warmed over a period of approximately forty minutes at 110° C. The reaction mixture was then cooled to ambient temperature, set aside overnight, rendered alkaline with 10 percent aqueous sodium hydroxide solution and extracted with benzene. Petroleum ether was slowly added to the separated benzene extract and the solid which slowly separated was collected by filtration and dried to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1-n-butyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R0 =R1 =R2 =R3 =Cl; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =(CH2)3CH3 ; Y1 =H), as white crystals having a melting point of 173°-175° C. The nuclear magnetic resonance spectrum was consistent with the structure; a maximum of 1770 cm-1 (C=O; s) appeared in the infrared spectrum; the spectrum showed a m/e peak at 617 (M+, 4 Cl).

Workup

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. extractionextracted with benzene
  3. additionPetroleum ether was slowly added to the separated benzene
  4. extractionextract
  5. customthe solid which slowly separated
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f5b939e32f764b718576b9f0f70bf53a
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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