Tert-Butylamine → 2-Chloro-4-methyl-thiazole-5-sulfonic acid tert-butylamide

HRID 1927985Notes

Reaction equation

HRID 1927985 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[S:8][C:9]([S:13](Cl)(=[O:15])=[O:14])=[C:10]([CH3:12])[N:11]=1>C([O-])(O)=O.[Na+].C(OCC)(=O)C>[C:1]([NH:5][S:13]([C:9]1[S:8][C:7]([Cl:6])=[N:11][C:10]=1[CH3:12])(=[O:15])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 120942502-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride

Product 1

HCID 434560622-Chloro-4-methyl-thiazole-5-sulfonic acid tert-butylamideYield 79.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of commercially available tert-butylamine (3.76 mL, 35.5 mmol) in saturated NaHCO3 solution (30 mL) and ethyl acetate (50 mL) was added at 0° C. (ice water bath) a solution of commercially available 2-chloro-4-methyl-thiazole-5-sulfonyl chloride [CAS-No. 292138-59-1] (5.0 g, 21.5 mmol). The reaction mixture was stirred at room temperature for 16 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 (4.57 g, 79%) as a yellow solid. MS (ISN) 267.3 [(M−H)−].

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-d59504cb4f78499ab1ac275097a8ab74
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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