Water → HCID 68777960, compound

HRID 2263033Notes

Reaction equation

HRID 2263033 reaction equation
[O:1]=[S:2]1(=[O:20])[C:6]2[CH:7]=[C:8]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[CH:9]=[CH:10][C:5]=2[CH:4]=[CH:3]1.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]1[N:30]=[C:29]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[S:28][N:27]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[O:20]=[S:2]1(=[O:1])[C:6]2[CH:7]=[C:8]([NH:11][C:12]([N:34]3[CH2:33][CH2:32][N:31]([C:29]4[S:28][N:27]=[C:26]([C:22]5[S:21][CH:25]=[CH:24][CH:23]=5)[N:30]=4)[CH2:36][CH2:35]3)=[O:19])[CH:9]=[CH:10][C:5]=2[CH:4]=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 68778015HCID 68778015, compoundHCID 866254872,2,2-Trichloroethyl (1,1-dioxido-1-benzothien-6-yl)carbamate

Product 1

HCID 68777960HCID 68777960, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl (1,1-dioxido-1-benzothien-6-yl)carbamate (257 mg, 0.720 mmol), 1-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine (200 mg, 0.792 mmol) and diisopropylethylamine (0.129 ml, 0.720 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Chloroform was added to the residue, and 69.6 mg (21.0%) of the desired product as a solid was separated by filtration.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionChloroform was added to the residue, and 69.6 mg (21.0%) of the desired product as a solid
  6. customwas separated by filtration

Sources & evidence

ORD record
ord-5cf900c58ab241ab9faaf550b72ec063
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…