Thiourea → HCID 23372674, compound

HRID 1899097Notes

Reaction equation

HRID 1899097 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:6]=1)=O.[NH2:27][C:28]([NH2:30])=[S:29]>C(O)C.C(Cl)(Cl)Cl>[NH2:30][C:28]1[S:29][CH:2]=[C:3]([C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:6]=2)[N:27]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 23372639HCID 23372639, compound

Product 1

HCID 23372674HCID 23372674, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 5-(bromoacetyl)-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (2 g) and thiourea (0.61 g) in ethanol (80 ml) was refluxed for 30 minutes. The mixture was dissolved in chloroform, washed with an aqueous solution of sodium bicarbonate and water, dried, and concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (10:1) to give pale yellow crystals to 5-(2-amino-4-thiazolyl)-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (0.62 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. washwashed with an aqueous solution of sodium bicarbonate and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (10:1)

Sources & evidence

ORD record
ord-a4b8d3e8c035473f8a7da1205ffe41fe
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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