Thionyl Chloride → N-(Butan-2-yl)-N-methyl-4-phenylnaphthalene-2-carboxamide

HRID 615385Notes

Reaction equation

HRID 615385 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17](O)=[O:18])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:24][NH:25][CH:26]([CH2:28][CH3:29])[CH3:27]>N1C=CC=CC=1>[CH3:24][N:25]([CH:26]([CH3:27])[CH2:28][CH3:29])[C:17]([C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=[O:18]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 111026N-Methyl-2-butanamineHCID 132723484-Phenylnaphthalene-2-carboxylic acid

Product 1

HCID 13272352N-(Butan-2-yl)-N-methyl-4-phenylnaphthalene-2-carboxamideYield 54.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Operations are carried out as for Example 1, starting from 4.3 g of 4-phenyl naphthalene 2-carboxylic acid, 20 ml of thionyl chloride and then 1.5 g of N-methyl 2-butanamine in 20 ml of pyridine. 3 g of N-methyl N(1-methyl propyl) 4-phenyl naphthalene 2-carboxamide, melting at 108° C., are obtained.

Sources & evidence

ORD record
ord-489f312cf48c49a8af7936658bcd88e4
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Reaction notes

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