Sodium Hydroxide → HCID 90405349, compound

HRID 924250Notes

Reaction equation

HRID 924250 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH2:21][CH3:22])=[C:6]([NH:8][C:9]([NH:11]C(=O)C2C=CC=CC=2)=[S:10])[CH:7]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH2:21][CH3:22])=[C:6]([NH:8][C:9]([NH2:11])=[S:10])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90404478HCID 90404478, compound

Product 1

HCID 90405349HCID 90405349, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To N-((5-methyl-2-propylphenyl)carbamothioyl)benzamide (C72) (3.21 g, 10.3 mmol) in methanol (80 mL) was added sodium hydroxide (2 N, 10.3 mL, 20.5 mmol) and heated at 50° C. for 2 hours and then stirred at room temperature over the weekend. The reaction was concentrated, diluted with water, extracted with dichloromethane, filtered through a phase separator, concentrated, and dried in a vacuum oven to provide the title compound as a tan solid (1.80 g, 83%): mp 143-145° C.; 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.20 (d, J=7.8 Hz, 1H), 7.12 (dd, J=7.8, 1.2 Hz, 1H), 7.04 (s, 1H), 5.99 (d, J=254.5 Hz, 2H), 2.57 (d, J=7.5 Hz, 2H), 2.33 (s, 3H), 1.59 (dq, J=14.8, 7.4 Hz, 2H), 0.95 (t, J=7.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 181.96, 137.53, 136.74, 134.00, 130.69, 129.72, 127.85, 32.90, 23.66, 20.80, 13.93; ESIMS m/z 209 ([M+H]+).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. filtrationfiltered through a phase separator
  5. concentrationconcentrated
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1152a0938717481bada35c73d4f7a7d9
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

Loading…