3,5-Dimethylbenzenethiol → HCID 19365875, compound

HRID 849989Notes

Reaction equation

HRID 849989 reaction equation
C[C:2]1[C:3]([S:12][C:13]2[CH:18]=[C:17](C)[CH:16]=[C:15](C)[CH:14]=2)=[C:4]([N+]([O-])=O)[C:5](=[O:8])[NH:6][CH:7]=1.C(C1C(SC2C=C(C)C=C(C)C=2)=C(C(OCC)=O)C(=O)NC=1C)C.CC1C=C(S)C=C(C)C=1>C(O)C.C(N(CC)CC)C>[C:13]1([S:12][C:3]2[CH:2]=[CH:7][NH:6][C:5](=[O:8])[CH:4]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 1175483,5-DimethylbenzenethiolHCID 4645742(1H)-Pyridinone, 4-((3,5-dimethylphenyl)thio)-5-methyl-3-nitro-HCID 4646013-Pyridinecarboxylic acid, 4-((3,5-dimethylphenyl)thio)-5-ethyl-1,2-dihydro-6-methyl-2-oxo-, ethyl ester

Product 1

HCID 19365875HCID 19365875, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

As for the method described for obtaining compound 7a in example 10, a mixture of compound 15 (1.00 g, 4.1 mmoles) in 10 ml of ethanol and 1 ml of triethylamine was agitated until homogeneous. 3,5-dimethylthiophenol (0.61 ml, 4.5 mmoles) was added. After 12 hours under reflux, the white precipitate was isolated by filtration and crystallised in ethyl acetate. Product 15 was obtained (1.05 g, 82%) in the form of white crystals: melting point 202° C.; NMR-1H (DMSO-d6) δ 12.17 (1H, s, NH-1), 7.22 (1H, s, H-4'), 6.92 (1H, s, H-2' and 6'), 4.09 (2H, q, J=7 Hz, COOCH2CH3), 2.45 (2H, q, J=7 Hz, CH2CH3), 2.27 (3H, s, CH3 -6), 2.25 (6H, s, CH3 -3' and 5'), 1.15 (3H, t, j=7 Hz, COOCH2CH3), 0.85 (3H, t, J=7 Hz, CH2CH3). Anal. C19H23NO3S (C, H, N, S).

Workup

  1. temperatureAfter 12 hours under reflux
  2. customthe white precipitate was isolated by filtration
  3. customcrystallised in ethyl acetate

Sources & evidence

ORD record
ord-14b2803ebb0548299d13cc08434af730
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

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