Ethanol → HCID 68559639, compound

HRID 1028920Notes

Reaction equation

HRID 1028920 reaction equation
C(O)C.[N+:4]([C:7]1[CH:46]=[CH:45][C:10](/[CH:11]=[CH:12]/[CH:13]([S:22]([CH:25](/[CH:34]=[CH:35]/[C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][CH:37]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)(=[O:24])=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)([O-])=O.O.NN>[Pd].C(Cl)(Cl)Cl>[NH2:4][C:7]1[CH:46]=[CH:45][C:10](/[CH:11]=[CH:12]/[CH:13]([S:22]([CH:25](/[CH:34]=[CH:35]/[C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)(=[O:23])=[O:24])[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 86642669HCID 86642669, compound

Product 1

HCID 68559639HCID 68559639, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

In a 100 mL round-bottomed flask fitted with condenser, 5% Pd/C (0.073 g) was taken and 20 mL ethanol was added slowly. Compound 6d (0.5 g, 1.4 mmol) and hydrazine hydrate (1.24 g, 38.7 mmol) were added to the content of the flask and refluxed for 6 h. Completion of the reaction was monitored by TLC (CHCl3 on silica gel plate), filtered the reaction mixture through celite and concentrated the reaction mixture to 50% volume. The concentrated mixture was poured onto crushed ice, the solid formed was filtered, washed with cooled water, dried to get the desired product 6e. Yield: 52%; light yellow solid mp 164-168° C. 1H NMR: δ 3.80 (s, 3H, OCH3), 4.22 (s, 2H, CH2), 4.04 (br s, 2H, NH2), 6.42 (d, 1H, J=15.6 Hz, ═CH), 6.60-7.31 (m, 9H, Ar—H+ vinylic). Anal. (C16H17NO3S): C, H, N.

Workup

  1. customIn a 100 mL round-bottomed flask fitted with condenser
  2. temperaturerefluxed for 6 h
  3. filtrationfiltered the reaction mixture through celite and
  4. concentrationconcentrated the reaction mixture to 50% volume
  5. additionThe concentrated mixture was poured
  6. customonto crushed ice
  7. customthe solid formed
  8. filtrationwas filtered
  9. washwashed with cooled water
  10. customdried

Sources & evidence

ORD record
ord-b46647d9abe24a728ccf0cf8f900859a
Source dataset
uspto-grants-2014_05
Patent number
US08735620B2

Reaction notes

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