Hydrochloric Acid → HCID 18968882, compound

HRID 398816Notes

Reaction equation

HRID 398816 reaction equation
[NH2:1][C:2]([CH2:23][OH:24])([CH2:21][CH3:22])[CH2:3][S:4]([C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(=[O:6])=[O:5].Cl>N1C(C)=CC=CC=1C.C(OCC)C>[CH2:21]([C:2]1([CH2:23][OH:24])[N:1]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[S:4](=[O:6])(=[O:5])[CH2:3]1)[CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18968841HCID 18968841, compound

Product 1

HCID 18968882HCID 18968882, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 79372,6-LutidineSolvent

Procedure

The product from step (b) (38.7 g) was dissolved in 600 ml of 2,6-lutidine and 120 ml of 1.0M HCl in diethyl ether was then added. The reaction mixture was refluxed overnite, using a Dean Stark trap, then concentrated in vacuo. The residue was taken up in 5% NaHCO3 whereupon solidification took place. The solids were filtered and washed with ether to afford the desired product as a light brown solid (25.7 g), mp 170°-171° C. 1H NMR consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was refluxed overnite
  2. concentrationconcentrated in vacuo
  3. filtrationThe solids were filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-fec9d846870d4f28ba71127690a114b0
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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