Sodium Hydroxide → HCID 90413532, compound

HRID 924283Notes

Reaction equation

HRID 924283 reaction equation
C(NC(/[N:6]=[C:7]1/[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH3:22])[C:9](=[O:14])[N:10]([CH2:12][CH3:13])[S:11]/1)=O)C.[OH-].[Na+]>CO>[CH2:12]([N:10]1[C:9](=[O:14])[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH3:22])[C:7](=[NH:6])[S:11]1)[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90412717HCID 90412717, compound

Product 1

HCID 90413532HCID 90413532, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-1-Ethyl-3-(2-ethyl-4-(2-ethylphenyl)-3-oxo-1,2,4-thiadiazolidin-5-ylidene)urea (CB42) (0.484 g, 1.51 mmol) was dissolved in methanol (150 mL). Sodium hydroxide (3.36 g, 84.0 mmol) was slowly added and the reaction was stirred at room temperature. After 4 hours the solution was concentrated to ½ volume, poured onto water, and extracted with ethyl acetate. The organics were dried and concentrated to give the title compound as an orange solid (0.249 g, 65%): 1H NMR (400 MHz, CDCl3) δ 7.35-7.32 (m, 2H), 7.30 (dd, J=5.4, 1.5 Hz, 1H), 7.25-7.20 (m, 1H), 3.65 (q, J=7.2 Hz, 2H), 3.39-3.19 (m, 1H), 2.73 (q, J=7.6 Hz, 2H), 1.26-1.13 (m, 6H); 13C NMR (101 MHz, CDCl3) δ 173.32, 165.49, 141.20, 135.74, 130.42, 129.31, 127.67, 126.01, 39.50, 24.79, 15.22, 14.93; ESIMS m/z 250 ([M]+).

Workup

  1. concentrationAfter 4 hours the solution was concentrated
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. customThe organics were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a46c26dba82644e985dec60547b4c8b1
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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