Water → 3-(2-amino-6-chlorobenzothiazol-5-yl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 621366Notes

Reaction equation

HRID 621366 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([N:8]2[N:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[O:10][C:9]2=[O:17])[CH:7]=1.[S-:19][C:20]#[N:21].[NH4+].BrBr.O>C(O)(=O)C>[NH2:21][C:20]1[S:19][C:3]2[CH:4]=[C:5]([Cl:18])[C:6]([N:8]3[N:12]=[C:11]([C:13]([CH3:15])([CH3:14])[CH3:16])[O:10][C:9]3=[O:17])=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 142806573-(5-Amino-2-chlorophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 142806583-(2-amino-6-chlorobenzothiazol-5-yl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-oneYield 84.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(5-Amino-2-chlorophenyl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (38.28 g) was dissolved in 95% acetic acid (138.20 g), and ammonium thiocyanate (27.64 g) was added thereto, followed by stirring at room temperature for 3 hours. To the resultant mixture, a solution of bromine (27.64 g) in acetic acid (41.46 g) was added, followed by stirring at room temperature for 12 hours. The reaction mixture was combined with hot water (274.7 ml), heated to 100° C. and filtered while hot. The filtrate was neutralized with sodium carbonate and extracted with ethyl acetate. Teh extract was washed with water, dried and distilled under reduced pressure to give 3-(2-amino-6-chlorobenzothiazol-5-yl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (39.06 g) as a resinous substance.

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. temperatureheated to 100° C.
  3. filtrationfiltered while hot
  4. extractionextracted with ethyl acetate
  5. extractionTeh extract
  6. washwas washed with water
  7. customdried
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-20411e165fc74c1d810ec44f7cf122cd
Source dataset
uspto-grants-1989_04
Patent number
US04824465

Reaction notes

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