Sodium Hydroxide → methyl N-[2-(2,4-dichlorophenoxy)acetyl]carbamimidate

HRID 1284813Notes

Reaction equation

HRID 1284813 reaction equation
S(O)(O)(=O)=O.[CH3:6][O:7][C:8](=[NH:10])[NH2:9].[OH-].[Na+].[Cl:13][C:14]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18](Cl)=[O:19]>O.C(Cl)Cl>[Cl:13][C:14]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18]([NH:10][C:8](=[NH:9])[O:7][CH3:6])=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)

Product 1

HCID 140341272methyl N-[2-(2,4-dichlorophenoxy)acetyl]carbamimidate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

13.5 g (0.11 mole) of O-methyl-isourea sulfate are dissolved in 50 ml of water and 100 ml of methylene chloride. 16 g of 50% strength aqueous sodium hydroxide solution (0.2 mole) and 24 g (0.1 mole) of 2,4-dichlorophenoxyacetyl chloride are simultaneously added dropwise from two separate vessels at 0° C., with vigorous stirring. The mixture is stirred at 0° C. for 1 hour and at 40° C. for 3 hours and the organic phase is separated off, washed twice with 100 ml of water and dried over sodium sulfate.

Workup

  1. customseparate vessels at 0° C.
  2. customthe organic phase is separated off
  3. washwashed twice with 100 ml of water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c5ce6949783141e28390a850f73e4a0f
Source dataset
uspto-grants-1986_01
Patent number
US04564382

Reaction notes

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