Sulfuric Acid → HCID 59208499, compound

HRID 2243046Notes

Reaction equation

HRID 2243046 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[S:8][C:9]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:10]([CH2:12][OH:13])[N:11]=1.C([OH:23])(C)C>CC(C)=O.O.[Na+].[Cl-]>[Cl:6][C:7]1[S:8][C:9]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:10]([C:12]([OH:23])=[O:13])[N:11]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 59208454HCID 59208454, compound2×

Product 1

HCID 59208499HCID 59208499, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 5234Sodium ChlorideSolvent

Procedure

A solution of 3 mL H2SO4 and 12 mL water were cooled in an ice water bath, and 2.3 g (23 mmol) CrO3 was added portionwise. The solution was added dropwise to a cooled (ice water bath) solution of 2.74 g (11.6 mmol) of isopropyl 2-chloro-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate (Intermediate 13) in acetone (50 mL) The resulting mixture was stirred 4 hours with warming to room temperature. Isopropanol (2 mL) was added and stirring was continued for 15 min. The solution was diluted with water, saturated with NaCl and extracted 3 times with EtOAc. The EtOAc was washed with brine, dried (MgSO4) and concentrated to give 2.86 g of an oil. NMR: 1.3 (d, 6H), 5.1 (m, 1H), 14.1 (s, 1H).

Workup

  1. additionThe solution was added dropwise to
  2. stirringstirring
  3. waitwas continued for 15 min
  4. extractionextracted 3 times with EtOAc
  5. washThe EtOAc was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d1206431c0af4c18bf0fcf3b2ca017f3
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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