1-benzoyl-3-(2-(4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)phenyl)thiourea → N-[2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)phenyl]thiourea

HRID 2192214Notes

Reaction equation

HRID 2192214 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH3:30])([CH3:29])[CH2:21][CH2:20]1)=[S:11])(=O)C1C=CC=CC=1>CO>[CH3:29][C:22]1([CH3:30])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:10]([NH2:9])=[S:11])[CH2:20][CH2:21]1

Participants

3

Reactant 1

HCID 593376891-benzoyl-3-(2-(4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)phenyl)thiourea

Product 1

HCID 59337688N-[2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)phenyl]thiourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1e was heated at 80° C. in the presence of MeOH (2.5 mL and 1N NaOH 0.5 mL) for 40 min. LC-MS showed completion of the reaction. The solvent was concentrated, and 1N HCl was added followed by the addition of Et2O. The Et2O layer was separated and was washed with H2O (2×), brine, dried over MgSO4, filtered, and concentrated to dryness. The resulting crude if was used directly in the next step: LC-MS (ESI) 312.1 (M+H) (10-90% MeOH in H2O with 0.1% TFA in a 4 min run, tR=3.51 min).

Workup

  1. customcompletion of the reaction
  2. concentrationThe solvent was concentrated
  3. addition1N HCl was added
  4. additionfollowed by the addition of Et2O
  5. customThe Et2O layer was separated
  6. washwas washed with H2O (2×), brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cf012dd7d74e41659d6bca23db028843
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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