1,2-Dichloroethane → HCID 18616053, compound

HRID 1263409Notes

Reaction equation

HRID 1263409 reaction equation
[Cl:1][N:2]1[C:6]2[C:7]([CH3:14])=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][CH2:3]1.[CH3:15][N:16]1[C:20](O)=[CH:19][CH:18]=[N:17]1.C(#N)C.C(Cl)CCl>CN(C1C=CN=CC=1)C.O.C(N(CC)CC)C>[Cl:1][N:2]1[C:6]2[C:7]([CH3:14])=[C:8]([C:11]([O:13][C:20]3[N:16]([CH3:15])[N:17]=[CH:18][CH:19]=3)=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][CH2:3]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 6342AcetonitrileHCID 18616030HCID 18616030, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 18616053HCID 18616053, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

1 g of 3-chloro-4-methylbenzothiazol-5-carboxylic acid (4.4 mol) and 0.46 g of 1-methyl-5-hydroxypyrazole (4.7 mol) were dissolved in 50 ml of abs. acetonitrile and admixed with 1 g of EDC, 0.7 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the product was extracted with ethyl acetate. The organic phase was washed and dried and the product was purified by crystallization/column chromatography. Yield: 0.22 g (16%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic phase was washed
  3. customdried
  4. customthe product was purified by crystallization/column chromatography

Sources & evidence

ORD record
ord-0e927be09fb34b51bea0202baafbd83b
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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