Acetic Anhydride → 3-[2,4-Bis(dimethylamino)phenyl]-3-(9-ethyl-3-carbazolyl)phthalide

HRID 1703230Notes

Reaction equation

[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]([OH:22])=[O:21])=O)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[CH3:27][N:28]([CH3:38])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=1.C(OC(=O)C)(=O)C>>[CH3:36][N:35]([CH3:37])[C:31]1[CH:30]=[C:29]([N:28]([CH3:38])[CH3:27])[CH:34]=[CH:33][C:32]=1[C:16]1([C:12]2[CH:13]=[CH:14][C:15]3[N:3]([CH2:1][CH3:2])[C:4]4[C:9]([C:10]=3[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:18]2[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:20](=[O:22])[O:21]1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-

HCID 204713592-(9-Ethyl-9H-carbazole-3-carbonyl)benzoic acid

Product 1

HCID 205235423-[2,4-Bis(dimethylamino)phenyl]-3-(9-ethyl-3-carbazolyl)phthalide

Procedure

A mixture of 3.43 g (0.01 mole) of 2-[(9-ethyl-3-carbazolyl)carbonyl]benzoic acid, 1.80 g (0.011 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and 4.0 ml of acetic anhydride was interacted in a manner similar to that described in Example 1, part C above to yield 3-[2,4-bis(dimethylamino)phenyl]-3-(9-ethyl-3-carbazolyl)phthalide (Formula V: R0 =R1 =R2 =R3 =H; R=CH3 ; R4 =N(CH3)2 ; R8 =CH2CH3) which melted over the range 134°-142° C. A significant infrared absorption maximum appeared at 1753 cm-1 (C=O; s). A toluene solution of this product spotted on silica gel developed a bordeaux-colored image.

Sources & evidence

ORD record: ord-57244182c09b4984a90004b7fe40bccb
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351768

Reaction notes

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