Sodium Hydroxide → HCID 10633802, compound

HRID 327172Notes

Reaction equation

HRID 327172 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10707152HCID 10707152, compound

Product 1

HCID 10633802HCID 10633802, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-[(4-nitrophenyl)sulfonyl]thiazole (1.50 g, 5.6 mmol) and stannous chloride dehydrate (6.26 g, 27.7 mmol) in absolute ethanol (25 mL) was heated at reflux for 1 hour. The reaction mixture was poured into ice water, and the aqueous solution basified with 15% NaOH and extracted with ethyl acetate (2×200 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed to yield a solid which on trituration with diethyl ether and filtration yielded the title thiazole (1.21 g, 89%) as a pale yellow solid, mp 148°-150° C. 1H--NMR (250 MHz, d6 --DMSO): 6.44 (br s, 2H, NH2), 6.66 (d, 2H, J=8.8 Hz, aromatic), 7.61 (d, 2H, J=8.7 Hz, aromatic), 8.03 (d, 1H, J=3.2 Hz, aromatic), 8.14 (d, 1H, J=3.2 Hz, aromatic). MS (CI, CH4): 241(M+1).

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined organic portions were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto yield a solid which on trituration
  7. filtrationwith diethyl ether and filtration

Sources & evidence

ORD record
ord-0a6039b3f6484f6cb656af517799a80e
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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