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

HRID 1707150

Reaction equation

HRID 1707150 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-92da73be3588408d8cd7416d4ec2d01b
Source dataset
uspto-grants-1980_06
Patent number
US04209618

Linked notes

Loading…