Sodium Hydroxide → HCID 178510072, compound

HRID 258416Notes

Reaction equation

HRID 258416 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1)#[N:2].[NH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15].[OH-].[Na+:19]>C(#N)C.O>[Na:19][CH:13]([S:14]([OH:17])(=[O:16])=[O:15])[NH:12][C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)=[O:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 83791Aminomethanesulfonic acidHCID 1703804-Cyanophenyl isocyanate

Product 1

HCID 178510072HCID 178510072, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-cyanophenyl isocyanate (0.400 g, 2.78 mmol) in 5 mL of acetonitrile was added a solution of aminomethylsulfonic acid (0.308 g, 2.77 mmol) and sodium hydroxide (0.111 g, 2.78 mmol) in 1.5 mL of water. The reaction mixture was stirred for 4 days, then concentrated in vacuo. The residue was slurried in water, and filtered. The filtrate was concentrated in vacuo, slurried in acetonitrile and filtered to afford 0.67 g (99%) of crude product. The crude product was purified by recrystallization from ethanol/water to afford 0.423 g (62%) of the desired urea. Analytical results are given below.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered
  5. customto afford 0.67 g (99%) of crude product
  6. customThe crude product was purified by recrystallization from ethanol/water

Sources & evidence

ORD record
ord-23c0119b14e548a1ae7161d8808512ae
Source dataset
uspto-grants-1993_11
Patent number
US05266717

Reaction notes

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