Chloroacetic Acid → HCID 18625228, compound

HRID 1859377Notes

Reaction equation

HRID 1859377 reaction equation
[CH2:1]([N:5]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][CH:11]=1)=[S:7])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl[CH2:28]C(O)=O>O>[CH2:1]([N:5]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1[S:7][CH:28]=[C:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][CH:11]=2)[N:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 18823139HCID 18823139, compound2×

Product 1

HCID 18625228HCID 18625228, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 174.15 g (0.50 mol) of N,N-di-n-butyl-N′-(4-t-butylbenzoyl)thiourea (compound 1-2), 44.0 g (1.10 mol) of sodium hydroxide and 500 ml of water was added 56.70 g (0.60 mol) of chloroacetic acid. The mixture was stirred and heated on a steam bath for 22 hrs and cooled. The water phase was decanted from the solid phase, and the solid was washed with water and methanol. Recrystallization of the solid from methanol gave 85.6 g (49.7% yield) of product; mp: 48.5-49.5° C. The NMR spectrum was consistent with the proposed structure. Anal. Calcd. for C21H32N2S: C, 73.20; H, 9.36; N, 8.13; S, 9.30. Found: C, 73.04; H, 9.29; N, 8.02; S, 9.19.

Workup

  1. temperatureheated on a steam bath for 22 hrs
  2. temperaturecooled
  3. customThe water phase was decanted from the solid phase
  4. washthe solid was washed with water and methanol
  5. customRecrystallization of the solid from methanol

Sources & evidence

ORD record
ord-25628e18afca447b9090904f78886bdc
Source dataset
uspto-grants-2003_03
Patent number
US06528223B1

Reaction notes

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