Hydrochloric Acid → HCID 54025116, compound

HRID 482702

Reaction equation

HRID 482702 reaction equation
[O:1]=[C:2]([CH2:4][N:5]([C:7](=[NH:9])[NH2:8])[CH3:6])[OH:3].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:28][C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1.Cl>CO.CN(C=O)C.O>[NH2:9][C:7](=[N:8][C:36]([NH:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[CH:30]=1)=[O:37])[N:5]([CH3:6])[CH2:4][C:2]([OH:3])=[O:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 586CreatineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 54025116HCID 54025116, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 9.58 g (0.073 mole) of anhydrous creatine in 96 ml (0.073 mole) of 0.76M tetrabutylammonium hydroxide in methanol was evaporated to an oil in vacuo. The residue was dissolved in 100 ml of DMF. An 11.2 g (0.073 mole) sample of m-chlorophenylisocyanate was added dropwise and the reaction was stirred for two hours. The mixture was poured into 200 ml of water and 73 ml of 1N HCl. The gummy precipitate was induced to crystallize by scratching. The solid was collected and triturated with tetrahydrofuran to give 6.6 g (30% yield) of light yellow solid N-{amino[(3-chlorophenyl)aminocarbonyl]iminomethyl}-N-methylglycine. A hydrochloride salt was prepared from conc. HCl to yield a pink solid, m.p. 228°-234° C.

Workup

  1. customto crystallize
  2. customThe solid was collected
  3. customtriturated with tetrahydrofuran

Sources & evidence

ORD record
ord-388581ef70954789afe2084c405d230e
Source dataset
uspto-grants-1986_03
Patent number
US04575514

Linked notes

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