tert-Butanol → 4-Chloro-1,3-thiazole-5-carboxylic acid

HRID 411647Notes

Reaction equation

HRID 411647 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7]=[O:8].CC(=CC)C.C([OH:18])(C)(C)C.[O-]Cl=O.[Na+]>O>[Cl:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([OH:18])=[O:8]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 145013174-Chloro-1,3-thiazole-5-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 221478404-Chloro-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring mixture of 10.3 g (69.8 mmol) 4-chloro-thiazole-5-carbaldehyde (Journal of the Chemical Society, Perkins Transactions, 1992, 973-978), 296 ml (2792 mmol) 2-methyl-2-butene, and 200 mL tertiary butanol was added a solution of 50.5 g (558 mmol) NaClO2, 50.2 g (419 mmol) NaH2PO4 in 300 mL of water, dropwise over 20 minutes. The reaction was stirred for 1 hour then concentrated to ⅓ volume via rotary evaporation. The remaining solution was acidified with 6N HCl with rapid stirring. The precipitated solid was filtered and air dried under high vacuum overnight to give 10.6 g of white solid.

Workup

  1. concentrationthen concentrated
  2. customvia rotary evaporation
  3. filtrationThe precipitated solid was filtered
  4. customair dried under high vacuum overnight

Sources & evidence

ORD record
ord-3c08cbfba7b64ddeb0ac8a91f86f539d
Source dataset
uspto-grants-2003_05
Patent number
US06559168B2

Reaction notes

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