Dimethylamine, hydrochloride → HCID 22729188, compound

HRID 2085127Notes

Reaction equation

HRID 2085127 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-7cee0e6c58cd4c70a0c43d6d021a0cff
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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