1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → HCID 20523549, compound

HRID 1660289Notes

Reaction equation

HRID 1660289 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][N:24]([CH3:34])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]([CH3:33])[CH3:32])[CH:26]=1>C(OC(=O)C)(=O)C>[CH3:32][N:31]([CH3:33])[C:27]1[CH:26]=[C:25]([N:24]([CH3:34])[CH3:23])[CH:30]=[CH:29][C:28]=1[C:12]1([C:8]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=[CH:10][CH:9]=2)[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:17])[O:18]1

Participants

4

Reactant 2

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 20523556HCID 20523556, compound

Product 1

HCID 20523549HCID 20523549, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 2.91 g (0.01 mole) of 2-[(1-phenyl-2-pyrrolyl)carbonyl]benzoic acid prepared in part A above, 2.34 g (0.017 mole) of 84.6 percent active N,N,N',N'-tetramethyl-m-phenylenediamine in 4.0 ml of acetic anhydride was interacted in a manner similar to that described in Example 1, part C to obtain 2.61 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(1-phenyl-2-pyrrolyl)phthalide (Formula IV: Ro =R1 =R2 =R3 =H; R=CH3 ; R4 =N(CH3)2 ; R7 =C6H5), a peach-colored powder melting at 193°-194° C. The infrared spectrum showed a maximum at 1760 cm-1 (C=O; s). A toluene solution of this product spotted on silica gel developed an immediate orange-red-colored image.

Sources & evidence

ORD record
ord-4ca2eb7eef234732afb4929054baa48c
Source dataset
uspto-grants-1981_12
Patent number
US04307018

Reaction notes

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