1,3-Dichloropropane → 1,3-Propanediyl bis(p-aminobenzoate)

HRID 1873098Notes

Reaction equation

HRID 1873098 reaction equation
[Na].[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[CH:5][CH:4]=1.[K+].Cl[CH2:14][CH2:15][CH2:16]Cl.[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O-:25])=[O:24])=[CH:21][CH:20]=1.[Na+]>CS(C)=O.CN1CCCC1=O.CN(C)C=O>[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:14][CH2:15][CH2:16][O:25][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([NH2:18])=[CH:20][CH:21]=2)=[O:8])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 88811,3-DichloropropaneHCID 517441Sodium 4-aminobenzoateHCID 5360545SodiumHCID 23663628Potassium 4-aminobenzoate

Product 1

HCID 933121,3-Propanediyl bis(p-aminobenzoate)Yield 91.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Japanese Kokai 58059949 A2 discloses the preparation of 1,3-propanediol-bis(p-aminobenzoate) by heating Cl(CH2)3R (R=Cl, Br) with sodium or potassium p-aminobenzoate in an aprotic dipolar solvent, e.g., dimethyl formamide, dimethyl sulfoxide, or N-methylpyrrolidone. Thus, 0.15 mol of Cl(CH2)3Cl was heated with 0.3 mol sodium p-aminobenzoate in dimethyl sulfoxide at 100° for three hours to give 91.5 percent 1,3-propanediol bis(p-aminobenzoate) of 97.4 percent purity as opposed to a 3 percent yield with ethylene glycol as solvent. Cl(CH2)nCl(n=2, 4, 5, 8), instead of Cl(CH2)3Cl, gave the corresponding alkylene bis(p-aminobenzoates) in much lower yield.

Sources & evidence

ORD record
ord-824f4425390948e3a9a7ecd7e802b651
Source dataset
uspto-grants-2000_08
Patent number
US06111129

Reaction notes

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