Acetonitrile → 6-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1,3,4]thiadiazin-2-one

HRID 1619959Notes

Reaction equation

HRID 1619959 reaction equation
Br[CH:2]([CH2:20][CH3:21])[C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)=O.[NH:22]([NH:24][C:25](=[S:33])[O:26]C1C=CC=CC=1)N.C(#N)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:20]([CH:2]1[S:33][C:25](=[O:26])[NH:24][N:22]=[C:3]1[C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)[CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 866890652-Bromo-1-(2-phenyl-benzoxazol-6-yl)-butan-1-oneHCID 86689066O-phenyl hydrazinethiocarbamate

Product 1

HCID 674623276-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1,3,4]thiadiazin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 mg (145 μmol) 2-bromo-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one, 60 mg (293 μmol) O-phenyl hydrazinethiocarbamate, 50 μl (363 μmol) TEA, 2 ml acetonitrile and 200 μl water are stirred together at 80° C. for 1 h. The reaction mixture is extracted with water and DCM. The org. phase is dried and the solv. is eliminated completely in vacuo. The residue is combined with 1 ml acetonitrile and 2 drops of water. 10 mg (53 μmol) para-toluenesulphonic acid monohydrate are added under argon and the mixture is also stirred for 1 h at RT under argon. Then it is left to react for 30 min under argon at 100° C. in the microwave. The reaction mixture is purified by RP-HPLC.

Workup

  1. extractionThe reaction mixture is extracted with water and DCM
  2. customphase is dried
  3. waitThen it is left
  4. customto react for 30 min under argon at 100° C. in the microwave
  5. customThe reaction mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-2469b6bc273641319c28b458d3bb27bb
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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