Triethylamine → HCID 86597246, compound

HRID 1160994Notes

Reaction equation

HRID 1160994 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl.[CH3:36][O:37][NH2:38].C(=O)([O-])O.[Na+]>ClCCl.C(Cl)(Cl)Cl.O>[CH3:36][O:37][NH:38][C:1]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[CH:18][CH:19]=1)=[O:2]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 86597246HCID 86597246, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Carbonyl-di-imidazole (1.62 g, 2 eq) is added to a solution cooled down to 0° C., of tert-butyl 4-aminophenylcarbamate (1.04 g) in anhydrous dichloromethane (100 ml). The mixture is taken to a temperature of 20° C. and is stirred at this temperature for 15 hours. Triethylamine (7 ml, 10 eq) followed by O-methylhydroxylamine hydrochloride (4.2 g, 10 eq) are successively added to the reaction medium cooled down to 0° C. After stirring for 3 hours at a temperature of approximately 20° C., water saturated with sodium hydrogen carbonate and chloroform is added to the mixture. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. in order to produce tert-butyl 4-{[(methoxyamino)carbonyl]amino}phenylcarbamate (1.33 g). A current of gaseous hydrochloric acid is passed through a suspension of this derivative in ethyl acetate until the reaction is complete. The precipitate obtained is filtered then washed with diethyl ether and dried in order to produce N-(4-aminophenyl)-N′-methoxyurea hydrochloride (1 g).

Workup

  1. customis taken to a temperature of 20° C.
  2. additionare successively added to the reaction medium
  3. additionis added to the mixture
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-55c259d5fd1d492e8ff949e657d66eda
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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