Tert-Butylamine → 2-Chloro-thiazole-5-sulfonic acid tert-butylamide

HRID 1927981Notes

Reaction equation

HRID 1927981 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[S:8][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][N:11]=1>C([O-])(O)=O.[Na+].C(OCC)(=O)C>[C:1]([NH:5][S:12]([C:9]1[S:8][C:7]([Cl:6])=[N:11][CH:10]=1)(=[O:14])=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 162289432-Chloro-1,3-thiazole-5-sulfonyl chloride

Product 1

HCID 434557712-Chloro-thiazole-5-sulfonic acid tert-butylamideYield 84%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of commercially available tert-butylamine (5.03 g, 68.8 mmol) in saturated NaHCO3 solution (35 mL) and ethyl acetate (17 mL) was added at 0° C. (ice water bath) a solution of 2-chloro-thiazole-5-sulfonyl chloride [CAS-No. 88917-11-7] (5.0 g, 22.9 mmol). The reaction mixture was stirred at room temperature for 2 h, ethyl acetate (50 mL) was added followed by extraction. The water layer was again extracted with ethyl acetate (50 mL). The combined organic layers were washed with 2N HCl solution (40 mL) and brine (40 mL), dried (MgSO4) and evaporated to yield the title compound (4.9 g, 84%) as a yellow solid. MS (ISN) 253.1 [(M−H)−], mp 75° C.

Workup

  1. extractionfollowed by extraction
  2. extractionThe water layer was again extracted with ethyl acetate (50 mL)
  3. washThe combined organic layers were washed with 2N HCl solution (40 mL) and brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-31de71ee021b438d8d4084c01d10bbe7
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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