2-Thiazolemethanol, alpha-methyl- (7CI,9CI) → HCID 22220759, compound

HRID 1836728Notes

Reaction equation

HRID 1836728 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[S:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]([OH:22])[CH3:21]>ClCCl.CCOCC>[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:17]1[CH:18]=[CH:19][S:15][C:16]=1[CH:20]([OH:22])[CH3:21]

Participants

5

Reactant 2

HCID 99892952-Thiazolemethanol, alpha-methyl- (7CI,9CI)HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 22220759HCID 22220759, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

O-(Mesitylenesulfonyl)hydroxylamine containing ca. 18% water (1.95 g, 1.60 g dry wt., ca. 7.4 mmole) was dissolved in dichloromethane (12 mL) and dried over Na2SO4 and filtered. This was added dropwise to a solution of 1-(2-thiazolyl)ethanol (0.8 g, 6.2 mmole) in dichloromethane (4 mL) at 0 C. After stirring an additional 12 hr at 4 C., the mixture was diluted with ether (13 mL) and stored at 4 C. for 1 hr. The supernatant was decanted from the syrupy precipitate, which was triturated with 1:1 dichloromethane-ether (10 mL) to yield a powder which was filtered out, washed with the same solvent, and dried to yield 1.71 g of the title compound, mp 105-107 C.

Workup

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. waitfor 1 hr
  4. customThe supernatant was decanted from the syrupy precipitate, which
  5. customwas triturated with 1:1 dichloromethane-ether (10 mL)
  6. customto yield a powder which
  7. filtrationwas filtered out
  8. washwashed with the same solvent
  9. customdried

Sources & evidence

ORD record
ord-bb2e18f27c12453ea828748c53964ac5
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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