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

HRID 27031Notes

Reaction equation

HRID 27031 reaction equation
[Cl: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>CO>[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: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[Cl:1])[C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:5]1)[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 233433832-(2-Chloro-4-(diethylamino)benzoyl)benzoic acid

Product 1

HCID 544736693-(2,4-Bis(diethylamino)phenyl)3-(2-chloro-4-(diethylamino)phenyl)phthalideYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-chloro-4-(diethylamino)benzoyl)benzoic acid (6.61 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (4.30 g.) and acetic anhydride (5 ml.) was allowed to stand overnight at room temperature, then diluted with methanol (10 ml.), affording 3-(2,4-bis(diethylamino)phenyl)-3-(2-chloro-4-(diethylamino)phenyl)phthalide (I: X=Y4 =(CH3CH2)2N, Y2 =Cl, Z4 =Z5 =Z6 =Z7 =H) (3.94 g., m.p. 141°-143° C.).

Sources & evidence

ORD record
ord-cb3f51f37f9745f391e48bbf6e31d9bc
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Reaction notes

Loading…