Methanol → HCID 15918697, compound

HRID 485116Notes

Reaction equation

HRID 485116 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.CO.N1C=CC=C[CH:31]=1>C(Cl)CCl>[CH3:31][O:10][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:23])[CH3:1])=[CH:8][CH:7]=2)[C:11]2[C:12](=[CH:16][C:17]([N:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=2)[C:13](=[O:15])[O:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 88936Benzoic acid, 5-(dimethylamino)-2-[4-(dimethylamino)benzoyl]-

Product 1

HCID 15918697HCID 15918697, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a manner similar to that described in Example 1 above, 5.2 g of 2-(4-dimethylaminophenyl)carbonyl-5-dimethylaminobenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine at ambient temperature overnight to obtain 4.5 g of 3-methoxy-3-(4-dimethylaminophenyl)-6-dimethylaminophthalide (Formula II: R0 =R=R2 =R5 =H; R1 =N(CH3)2 ; R4 =R4' =Y=CH3 ; X=O), a pale green-colored solid which melted over the range of 141° to 149° C. An infrared maximum appeared at 1770 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Analysis by mass spectrum showed m/e peaks at 326 (M+) and 295 (M+ --OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a green-colored image.

Sources & evidence

ORD record
ord-9975b75f4bbb427c93e500acc61a8226
Source dataset
uspto-grants-1985_08
Patent number
US04535172

Reaction notes

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