Acetic Anhydride → 3-(2,4-Bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide

HRID 27024

Reaction equation

HRID 27024 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])=[O:5].[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>O>[CH2:36]([N:33]([CH2:34][CH3:35])[C:29]1[CH:28]=[C:27]([N:26]([CH2:38][CH3:39])[CH2:24][CH3:25])[CH:32]=[CH:31][C:30]=1[C:4]1([C:3]2[CH:15]=[CH:16][C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:18][C:2]=2[CH3:1])[C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:5]1)[CH3:37]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamine

Product 1

HCID 867348983-(2,4-Bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (12.48 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (10.56 g.) and acetic anhydride (12 ml.) was warmed (at 40°±8° C.) during one hour, diluted with water (50 ml., then 100 ml.), adjusted to pH 4.6 and filtered. The filtrate was clarified with water and adjusted to pH 5.5. Recrystallization of the resulting product (m.p. 134°-140° C.) from methanol afforded 3-(2,4-bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide (I: X=Y4 =(CH3CH2)2N, Y2 =CH3, Z4 =Z5 =Z6 =Z7 =H) (m.p. 149°-151° C.).

Workup

  1. temperaturewas warmed (at 40°±8° C.) during one hour
  2. filtrationfiltered
  3. customRecrystallization of the resulting product (m.p. 134°-140° C.) from methanol

Sources & evidence

ORD record
ord-fa66cc458c26455bb8925a70dd2f5bc7
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Linked notes

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