Dimethylamine → (E)-2-[(Dimethylamino)phenylmethylene]-benzo[b]thiophen-3(2H)-one

Reaction equation

[C:1]([C:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]=1[OH:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:25][NH:26][CH3:27]>>[CH3:25][N:26](/[C:1](/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:9]1\[C:10](=[O:18])[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[S:13]\1)[CH3:27]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24819Phosphorus pentachloride

HCID 4712192Methanone, (3-hydroxybenzo[b]thien-2-yl)phenyl-

Product 1

HCID 70479181(E)-2-[(Dimethylamino)phenylmethylene]-benzo[b]thiophen-3(2H)-oneYield 7%

Procedure

Prepared as in Example 1 from 2-benzoyl-benzo[b]thiophen-3-ol, phosphorus(V) chloride and 40% aqueous dimethylamine solution with a yield of 7% of theory.

Sources & evidence

ORD record: ord-4f8e862692ea491983956b96e1e7e580
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04288437

Reaction notes

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