Thiourea → HCID 86665174, compound

HRID 1893721Notes

Reaction equation

HRID 1893721 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=O)[CH2:14]Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[NH2:19][C:20]([NH2:22])=[S:21]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:19]=[C:20]([NH2:22])[S:21][CH:14]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 866423312-Bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethanone

Product 1

HCID 86665174HCID 86665174, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to Scheme 6, Step 1: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromoethanone (9.70 mmol, 3.00 g) and of thiourea (9.70 mmol, 739 mg) in acetone (20 mL) was stirred under reflux for 1 hour. After filtration and evaporation of the filtrate, the white solid was partitioned between EtOAc and a saturated solution of Na2CO3. The aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4, was filtered and was concentrated to yield 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-amine (8.14 mmol, 2.33 g) as an orange foam.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationAfter filtration and evaporation of the filtrate
  3. customthe white solid was partitioned between EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-72713a5767034d60b0ee9f0e8901310c
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

Loading…