Methanol → HCID 15918700, compound

HRID 1789274Notes

Reaction equation

HRID 1789274 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:14].S(Cl)(Cl)=O.CO.N1C=CC=C[CH:31]=1>C(Cl)CCl>[CH3:31][O:14][C:13]1([C:3]2[CH:4]=[CH:5][C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:7][C:2]=2[CH3:1])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=[O:19])[O:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acid

Product 1

HCID 15918700HCID 15918700, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Proceeding in a manner similar to that described in Example 1 above, 5.2 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic 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 to obtain 2.5 g of 3-methoxy-3-(2-methyl-4-diethylaminophenyl)phthalide (Formula II: R0 =R=R1 =R2 =H; R4 =R4' =C2H5 ; R5 =Y=CH3 ; X=O), a yellow-colored oil. A significant infrared maximum appeared at 1770 cm-1 (C=O; s). The nuclear magnetic resonance spectrum was concordant with the assigned structure. Analysis by mass spectrum showed m/e peaks at 325 (M+) and 294 (M+ -OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a yellow-colored image.

Sources & evidence

ORD record
ord-19d90ab0c1644f2d9508609f312bd603
Source dataset
uspto-grants-1987_08
Patent number
US04688059

Reaction notes

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