2-Aminothiazole → HCID 11458707, compound

HRID 1685289Notes

Reaction equation

HRID 1685289 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[S:11]1[CH:15]=[CH:14][N:13]=[C:12]1[NH2:16].[Na]>C1COCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:16][C:12]2[S:11][CH:15]=[CH:14][N:13]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 783082-Chloro-5-nitropyridineHCID 5360545Sodium

Product 1

HCID 11458707HCID 11458707, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chloro-5-nitropyridine (8.4 g, 53 mmol) and thiazol-2-amine (7.6 g, 76 mmol) in THF (250 mL) is cooled to 0° C. Sodium tert-butoxyde (30% w/w THF, 80 mL) is the added slowly over 15 minutes. The reaction mixture is then warmed slowly to room temperature and stirred 16 hours. The reaction mixture is then poured into a mixture of 1/1 ice/water (1.2 L) with stirring. The solid is filtered and air dried to give a powder (9.74 g, 83%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.17 (d, J=9.35 Hz, 2H), 7.20 (d, J=3.54 Hz, 1H), 7.49 (d, J=3.54 Hz, 1H), 8.43 (dd, J=9.35, 2.78 Hz, 1H), 9.15 (d, J=2.78 Hz, 1H), 12.17 (s, 1H). LCMS (M+H)+: 223.

Workup

  1. additionadded slowly over 15 minutes
  2. stirringwith stirring
  3. filtrationThe solid is filtered
  4. customair dried

Sources & evidence

ORD record
ord-72f4c10cd72b4a5a84fef5e287560901
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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