Acetic Anhydride → HCID 54075756, compound

HRID 27029Notes

Reaction equation

HRID 27029 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]1[CH:24]=[CH:23][C:7]([C:8]([C:10]2[C:18]([Cl:19])=[C:17]([Cl:20])[C:16]([Cl:21])=[C:15]([Cl:22])[C:11]=2[C:12]([OH:14])=[O:13])=O)=[CH:6][CH:5]=1)[CH3:2].[CH2:27]([N:29]([CH2:41][CH3:42])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH:31]=1)[CH3:28].C(OC(=O)C)(=O)C>CO>[CH2:39]([N:36]([CH2:37][CH3:38])[C:32]1[CH:31]=[C:30]([N:29]([CH2:41][CH3:42])[CH2:27][CH3:28])[CH:35]=[CH:34][C:33]=1[C:8]1([C:7]2[CH:23]=[CH:24][C:4]([N:3]([CH2:25][CH3:26])[CH2:1][CH3:2])=[CH:5][CH:6]=2)[C:10]2[C:11](=[C:15]([Cl:22])[C:16]([Cl:21])=[C:17]([Cl:20])[C:18]=2[Cl:19])[C:12](=[O:13])[O:14]1)[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 199566113,4,5,6-Tetrachloro-2-carboxy-4'-diethylaminobenzophenone

Product 1

HCID 54075756HCID 54075756, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (8.70 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (4.85 g.) and acetic anhydride (5 ml.) was heated (to 90° C.). Addition of methanol (10 ml.) and slurrying the resulting product with methanol (20 ml.) afforded 3-(2,4-bis(diethylamino)phenyl)-3-(4-(diethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X=Y4 =(CH3CH2)2N, Y2 =H, Z4 =Z5 =Z6 =Z7 =Cl) (7.85 g., m.p. 196°-197° C.).

Sources & evidence

ORD record
ord-0e1b4d6a5e7849f8a116e53f6702ef7e
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Reaction notes

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