Dimethylamine, hydrochloride → HCID 22729188, compound

HRID 460555Notes

Reaction equation

HRID 460555 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].COC1C=CC(C=CC(O)=O)=CC=1.S(Cl)(Cl)=O.Cl.[CH3:34][NH:35][CH3:36]>C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([N:35]([CH3:36])[CH3:34])=[O:8]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 132454-Methoxy cinnamic acidHCID 24386Thionyl ChlorideHCID 6931533-chloro-6-methoxy-1-benzothiophene-2-carboxylic acid

Product 1

HCID 22729188HCID 22729188, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

3.0 g of 3-chloro-6-methoxy-benzo(b)thiophene-2-carboxylic acid (7.0 g) synthesized from 4-methoxycinnamic acid (10.0 g) and thionyl chloride (15 ml) according to the method described in J. Med. Chem. 1992, 35, 958–965 was reacted with dimethylamine hydrochloride and triethylamine in THF to give the title compound (1.9 g) as a brown oil.

Sources & evidence

ORD record
ord-e6ecca9c52804f59a21fd25884d6de1b
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

Loading…