Hydrochloric Acid → HCID 16203464, compound

HRID 1825804Notes

Reaction equation

HRID 1825804 reaction equation
[CH3:1][Li].[C:3]1([C:17]([OH:19])=O)[C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.N#N.Cl>O1CCCC1.O>[C:3]1([C:17](=[O:19])[CH3:1])[C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14007272Thianthrene-1-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 16203464HCID 16203464, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (1.6M in ether, 57 ml, 90 mmol) was added drop wise to a stirred solution of thianthrene-1-carboxylic acid (11.71 g, 45 mmol) in dry tetrahydrofuran (200 ml) at −78° C. over 30 minutes under an inert atmosphere (N2). The reaction mixture was allowed to warm to room temperature and (very thick white suspension present) was left stirring for 4 hours. Water (10 ml) was then added carefully to the solution and the pH was adjusted to 1 (pH paper) with 2N HCl. The solvent was removed in vacuo and the yellow solid formed was filtered and dried overnight in a vacuum desiccators. The solid was then purified by column chromatography (ethyl acetate/hexane; 1:9) and was recrystalised from ethanol to give the desired product (6.58 g, 57%). 1HNMR (300 MHz, CDCl3): δH=2.65 (3H, s); 7.26 (3H, m); 7.47 (2H, m); 7.62 (2H, d). m/z (LC-MS, ESP) RT=4.95 min; (M++1)=259

Workup

  1. wait(very thick white suspension present) was left
  2. customThe solvent was removed in vacuo
  3. customthe yellow solid formed
  4. filtrationwas filtered
  5. customdried overnight in a vacuum desiccators
  6. customThe solid was then purified by column chromatography (ethyl acetate/hexane; 1:9)
  7. customwas recrystalised from ethanol

Sources & evidence

ORD record
ord-68461c620d2a4fa089695c882ff655b0
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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