Sodium Hydroxide → HCID 53781625, compound

HRID 2057413Notes

Reaction equation

HRID 2057413 reaction equation
[C:1]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[Na+].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.F[C:48]([N:50]([S:52][N:53]([C:55]([O:57][N:58]=[C:59]([S:61][CH3:62])[CH3:60])=[O:56])[CH3:54])[CH3:51])=[O:49]>O.C(Cl)Cl>[CH2:11]([O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][C:48]([N:50]([CH3:51])[S:52][N:53]([CH3:54])[C:55]([O:57][N:58]=[C:59]([S:61][CH3:62])[CH3:60])=[O:56])=[O:49])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 16330Butyl salicylateHCID 54165239HCID 54165239, compoundHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 53781625HCID 53781625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 5.8 g portion of n-butyl salicylate was added to a solution of 1.2 g of sodium hydroxide in 75 ml of water, producing a thick suspension. To the above suspension was added 100 ml of methylene chloride and 0.3 g of tricaprylylmethyl ammonium chloride. The reaction mixture was stirred vigorously while a solution of 8.1 g of methyl N-[[N-[(fluorocarbonyl-N-methylamino)thio]-N-methylaminocarbonyloxy]]ethanimidothioate in 50 ml methylene chloride was added dropwise. When addition was complete, stirring was continued for one hour. The organic phase was separated and washed with 200 ml of water followed by 100 ml of saturated sodium chloride solution. The organic solution was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. On scratching and standing, the crude reaction product partially solidified. The title compound was isolated by dissolving the crude reaction product in 25 ml of ethanol, cooling the solution and diluting with hexane to afford 5.7 g of 2-[N-methyl-N-[N-methyl-N-[(1-methylthioethylidene)aminooxycarbonyl]aminothio]aminocarbonyloxy]benzoic acid butyl ester, m.p. 87° -89° C. Absorption bands characteristic of the title compound were observed in the infrared and NMR spectrums.

Workup

  1. customproducing a thick suspension
  2. additionwas added dropwise
  3. additionWhen addition
  4. customThe organic phase was separated
  5. washwashed with 200 ml of water
  6. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled under reduced pressure
  8. customthe crude reaction product

Sources & evidence

ORD record
ord-9554b45789b843ec85959857526d640f
Source dataset
uspto-grants-1980_07
Patent number
US04210668

Reaction notes

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