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

HRID 1989262Notes

Reaction equation

HRID 1989262 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-be99882a282a46738ff3fbf73ea566e5
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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