Water → HCID 53995533, compound

HRID 477870Notes

Reaction equation

HRID 477870 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:16][C:17]1[S:18][C:19]([C:23]#[N:24])=[C:20]([NH2:22])[N:21]=1)[CH2:13][CH2:14][CH3:15].C(=O)(O)[O-].[Na+].[OH2:30]>C(Cl)Cl>[CH2:12]([S:16]([C:17]1[S:18][C:19]([C:23]#[N:24])=[C:20]([NH2:22])[N:21]=1)(=[O:9])=[O:30])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 542743064-Amino-2-(butylsulfanyl)-1,3-thiazole-5-carbonitrile

Product 1

HCID 53995533HCID 53995533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.0 g of 85% m-chloroperbenzoic acid are added in portions to a solution of 4.26 g of 2-n-butylthio-4-amino-5-cyanothiazole in 200 ml of methylene chloride, while stirring and at room temperature. After stirring overnight at room temperature an excess of sodium bicarbonate in water is added and the solution is stirred for one hour. The organic layer is separated, washed with water, dried, filtered and diluted with isopropanol. After distilling off a part of the methylene chloride the desired product crystallises: yield 4.34 g; melting-point 150°-152° C.; TLC: Rf (CH2Cl2) 0.05.

Workup

  1. additionis added
  2. stirringthe solution is stirred for one hour
  3. customThe organic layer is separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. additiondiluted with isopropanol
  8. distillationAfter distilling off a part of the methylene chloride the desired product
  9. customcrystallises
  10. custommelting-point 150°-152° C.

Sources & evidence

ORD record
ord-3d5b85b8c45244cab7d27dbfacd02146
Source dataset
uspto-grants-1989_12
Patent number
US04889863

Reaction notes

Loading…