Perchloric Acid → tert-Butyl {[(E)-{1-(2-amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene}amino]oxy}acetate

HRID 436531Notes

Reaction equation

HRID 436531 reaction equation
Cl(O)(=O)(=O)=O.C(OCCCCCCCCCCCC)(=O)C=C.CCCCCCCCCCCCC=C.[CH3:37][C:38]([O:41][C:42]([CH2:44][O:45]/[N:46]=[C:47](/[C:54]([S:56][C:57]1[S:65][C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[N:58]=1)=[O:55])\[C:48]1[N:52]=[C:51]([NH2:53])[S:50][CH:49]=1)=[O:43])([CH3:40])[CH3:39]>C(O)(=O)C>[CH3:40][C:38]([O:41][C:42]([CH2:44][O:45]/[N:46]=[C:47](/[C:54]([S:56][C:57]1[S:65][C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[N:58]=1)=[O:55])\[C:48]1[N:52]=[C:51]([NH2:53])[S:50][CH:49]=1)=[O:43])([CH3:37])[CH3:39]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 178460458HCID 178460458, compound

Product 1

HCID 13826572tert-Butyl {[(E)-{1-(2-amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene}amino]oxy}acetateYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After the flask is weighed (total weight yield); 201 g.), 183.6 g. of the reaction mixture are stripped under reduced pressure (up to about 150° C. at 0.5-1mm. Hg.) to give 96.2 g. of oligomer which corresponds to a weight yield of 52.4%. Analysis of the unstripped reaction mix by vapor phase chromatography and titration of the stripped oligomer using a standard perchloric acid solution in acetic acid gives the following final composition: Lauryl acrylate: tetradecene-1: BAEM 70.3:25.2:4.5 by weight. Kjeldahl nitrogen analysis gives a value of 0.39% N corresponding to 5.5% by weight of BAEM in the oligomer. Elemental analysis:

Workup

  1. custom(total weight yield)
  2. customup to about 150° C.
  3. custom) to give 96.2 g
  4. customAnalysis of the unstripped reaction
  5. additionmix by vapor phase chromatography and titration of the stripped oligomer
  6. customgives the following final composition

Sources & evidence

ORD record
ord-15fb7a731dc84adf9a00efb677691765
Source dataset
uspto-grants-1977_02
Patent number
US04009195

Reaction notes

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