Dimethylformamide diethylacetal → HCID 57082950, compound

HRID 1359010Notes

Reaction equation

[CH2:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[S:4](=[O:15])[CH2:3][CH2:2]1.C(O[CH:19](OCC)[N:20]([CH3:22])[CH3:21])C>>[CH3:19][N:20]([CH:22]=[C:3]1[CH2:2][CH2:1][C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[S:4]1=[O:15])[CH3:21]

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 123534822,3-Dihydro-4lambda~4~-naphtho[2,1-b]thiopyran-4(1H)-one

Product 1

HCID 57082950HCID 57082950, compound

Procedure

From 3-dimethylaminomethylenebenzo[f]thiochroman-4-one (400 mg, 1.26 mmol) and 4-(2-dimethylaminoethoxy)phenylguanidinium dinitrate (438 mg, 1.26 mmol) to afford the title compound (155 mg) as a canary yellow solid m.p. 165-167°. δH (CDCl3) 9.08 (1H, d, J 8.3 Hz), 8.38 (1H, s), 7.77 (2H, m), 7.55-7.46 (5H, m), 7.05 (1H, br s), 6.88 (2H, m), 4.05 (2H, t, J 5.8 Hz), 3.78 (2H, s), 2.73 (2H, t, J 5.8 Hz) and 2.34 (6H, s). MS (ES+) 429 (MH+). 3-Dimethylaminomethylenebenzo[f]thiochroman-4-one was prepared from benzo[f]thiochroman-4-one (1.50 g, 7.01 mmol) and N,N-dimethyl-formamide diethylacetal to give the compound as a yellow solid (1.67 g) m.p. 163-1650. MS(EI) 269 (M+, 49.8%), 82 (100%).

Sources & evidence

ORD record: ord-983c2f0758c54bfca4e8072401ee1448
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599908B1

Reaction notes

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