Acetic Anhydride → Fthalide

HRID 839360

Reaction equation

HRID 839360 reaction equation
CN(C)C1C=CC([C:7]([C:9]2[C:17]([Cl:18])=[C:16]([Cl:19])[C:15]([Cl:20])=[C:14]([Cl:21])[C:10]=2[C:11]([OH:13])=[O:12])=O)=CC=1.C(N(CC)C1C=CC=C(N(CC)CC)C=1)C.C(OC(=O)C)(=O)C>CO>[Cl:18][C:17]1[C:16]([Cl:19])=[C:15]([Cl:20])[C:14]([Cl:21])=[C:10]2[C:9]=1[CH2:7][O:12][C:11]2=[O:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 20287184HCID 20287184, compound

Product 1

HCID 33791Fthalide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
91 °C

Procedure

A mixture of 2-(4-(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (16.28 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (9.68 g.) and acetic anhydride (10 ml.) was heated (at 91° C.) during 2 hours. Addition of methanol (20 ml., then 12 ml., then 10 ml.) afforded 3-(2,4-bis-(diethylamino)phenyl)-3-(4-dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X = (CH3CH2)2N, Y2 = H, Y4 = (CH3)2N, Z4 = Z5 = Z6 = Z7 = Cl) in three fractions (m.p. 174°-176° C., m.p. 180°-181° C. and m.p. 180°-181° C.).

Sources & evidence

ORD record
ord-16bb0c203dd14fa7a151ef3fbe153254
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Linked notes

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