Acetic Anhydride → Fthalide

HRID 839359

Reaction equation

HRID 839359 reaction equation
C(N(CC)C1C=CC([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)=CC=1)C.CN(C)C1C=CC=C(N(C)C)C=1.C(OC(=O)C)(=O)C>CO>[Cl:19][C:18]1[C:17]([Cl:20])=[C:16]([Cl:21])[C:15]([Cl:22])=[C:11]2[C:10]=1[CH2:8][O:13][C:12]2=[O:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 199566113,4,5,6-Tetrachloro-2-carboxy-4'-diethylaminobenzophenone

Product 1

HCID 33791FthalideYield 103%

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'-tetramethyl-m-phenylenediamine (3.61 g.) and acetic anhydride (5 ml.) was heated (to 90° C.). Addition of methanol (10 ml.) and slurrying the resulting product with methanol afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(4-diethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X = (CH3)2N, Y2 = H, Y4 = (CH3CH2)2N, Z4 = Z5 = Z6 = Z7 = Cl) (5.60 g., m.p. 206°-207.5° C.).

Sources & evidence

ORD record
ord-1a6a548937a94484a44172645606ae00
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Linked notes

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