Water → HCID 88636139, compound

HRID 978789Notes

Reaction equation

HRID 978789 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[CH:20]=O.Cl.[NH2:23][OH:24].O>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[CH:20]=[N:23][OH:24]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 13393800HCID 13393800, compound

Product 1

HCID 88636139HCID 88636139, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

As in example 10 but starting with 1 g 4-chloro-3-formyl-8-methoxy-thioflav-3-ene in 1.5 ml DMF. 220 mg hydroxylamine hydrochloride dissolved in 2 ml DMF are added. After 11/2 hours of reflux, the solution is cooled at room temperature before the addition of 20 ml of water. After extraction with CH2Cl2 a gum is obtained which is purified by column chromatography on silicagel using n-hexane/acetone 9:1 as eluant. Pure 4-chloro-3-hydroxyiminomethyl-8-methoxy-thioflav-3-ene is obtained as a yellow solid. TLC (SiO2, n-hexane/acetone 4:1): Rf =0.15.-NMR (90 MHz, CDCl3): δ(ppm)=3.76 (s, 3H, OCH3), 5.5 [s, 1H, H-C(2)], 6.76-7.69 [m, 3H, H-C(5,6,7)], 7.17 [s, 5H, H-C(2',3',4',5',6')], 8.53 [s, 1H, CH=N], 11.4 [s, 1H, OH].-M.p. 190°-203° C. (n-hexane/toluene).

Workup

  1. additionare added
  2. temperatureAfter 11/2 hours of reflux
  3. extractionAfter extraction with CH2Cl2 a gum
  4. customis obtained which
  5. customis purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-77d055f4d1694aaeae52921df32bd350
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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