Pyridine → 4-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide

HRID 252240

Reaction equation

HRID 252240 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[S:5][C:6]=1[Cl:7].N1C=CC=CC=1.[O-:18][C:19]#[N:20].[Na+].Br.[Br:23][C:24]1[S:28][C:27]([NH2:29])=[N:26][CH:25]=1>C(#N)C.C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:20][C:19](=[O:18])[NH:29][C:27]2[S:28][C:24]([Br:23])=[CH:25][N:26]=2)(=[O:10])=[O:9])[S:5][C:6]=1[Cl:7]

Participants

8

Reactant 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 27972204-Bromo-5-chlorothiophene-2-sulfonyl chloride

Product 1

HCID 247523614-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-Bromo-5-chloro-thiophene-2-sulfonyl chloride (0.44 g, 1.50 mmol) and pyridine (0.27 ml, 3.40 mmol) were added to a stirred suspension of sodium cyanate (0.14 g, 2.20 mmol) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 4 hours. 5-Bromo-thiazol-2-ylamine hydrobromide (0.26 g, 1.00 mmol) was added and the reaction stirred for 30 minutes. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was filtered and the solid washed with water, cold methanol and diethyl ether. The solid was dried under reduced pressure to give 4-bromo-N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-5-chlorothiophene-2-sulfonamide, 0.29 g (60%), m/e 477.8 (MH−).

Workup

  1. stirringthe reaction stirred for 30 minutes
  2. filtrationThe resulting precipitate was filtered
  3. washthe solid washed with water, cold methanol and diethyl ether
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-b7e58246bbc2468bb2c288d11cb2e1de
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Linked notes

Loading…