Urea, 1-isopropyl-2-thio- → 4-(2-Isopropylamino-thiazol-4-yl)-benzoic acid

HRID 606601Notes

Reaction equation

HRID 606601 reaction equation
[CH:1]([NH:4][C:5]([NH2:7])=[S:6])([CH3:3])[CH3:2].Br[CH2:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=O>C1COCC1>[CH:1]([NH:4][C:5]1[S:6][CH:9]=[C:10]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[N:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1711921Urea, 1-isopropyl-2-thio-HCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 598073424-(2-Isopropylamino-thiazol-4-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isopropyl-thiourea (2.47 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.47 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The volume was reduced to 5 mL and the mixture was then cooled to −20° C. and filtered. The solid was washed with a small amount of diethylether and dried. m/z=263.1 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Workup

  1. temperaturewas heated to 80° C. for 2 hours
  2. temperaturethe mixture was then cooled to −20° C.
  3. filtrationfiltered
  4. washThe solid was washed with a small amount of diethylether
  5. customdried
  6. customused in the next step without any further purification

Sources & evidence

ORD record
ord-0573f6c1e87e49fd889133bfcccb7c37
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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