Dimethylformamide diethylacetal → 6-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one

HRID 1358996Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2=[O:12].C(O[CH:16](OCC)[N:17]([CH3:19])[CH3:18])C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9]([S:8][CH2:7][C:6](=[CH:16][N:17]([CH3:19])[CH3:18])[C:5]2=[O:12])=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 2480656-Chlorothiochroman-4-one

Product 1

HCID 38135366-chloro-2,3-dihydro-3-dimethylaminomethylene-4H-1-benzothiopyran-4-one

Procedure

The 7-chloro-3,4-dihydro-2-(dimethylaminomethylene)-4-thia-1(2H)-naphthalenone starting material was prepared from 6-chloro-thiochroman-4-one (3.97 g, 20 mmol) and N,N-dimethylformamide diethyl acetal (20 ml, 80 mmol) to give the desired product as yellow crystals (4.38 g) m.p. 127-128°. MS (ES+) 256 (MH+, 37Cl, 33%), 254 (MH+, 35Cl, 100%).

Sources & evidence

ORD record: ord-97145b46c0a344e3a421736abcac3474
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599908B1

Reaction notes

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