Trifluoroacetic acid → 2-Methyl-4-o-tolyl-thiazol-5-ylamine

HRID 474354Notes

Reaction equation

HRID 474354 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:13][C:11]1[S:12][C:8]([NH2:7])=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58063499(2-Methyl-4-o-tolyl-thiazol-5-yl)-carbamic acid tert-butyl ester

Product 1

HCID 580630422-Methyl-4-o-tolyl-thiazol-5-ylamineYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-methyl-4-o-tolyl-thiazol-5-yl)-carbamic acid tert-butyl ester (340 mg, 1.12 mmol, 1.0 equiv) in dichloromethane (10 mL) was treated with trifluoroacetic acid (0.7 mL, 9.00 mmol, 8.0 equiv) for 24 hours at ambient temperature. The mixture was concentrated under vacuum and the resultant residue dissolved in dichloromethane and washed sequentially with 10% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The collected organic was dried over magnesium sulfate and filtered. The filtrate was passed through an Isolute® SCX-2 cartridge (eluting with dichloromethane, dichloromethane/methanol (1:1) and 2M ammonia in methanol) to afford 62.0 mg (27%) of 2-methyl-4-o-tolyl-thiazol-5-ylamine as a brown residue. LCMS (ESI) m+H=205.0; 1H NMR (400 MHz, CDCl3) δ: 7.33-7.18 (m, 4H), 3.54-3.45 (br, 2H), 2.58 (s, 3H), 2.29 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe resultant residue dissolved in dichloromethane
  3. washwashed sequentially with 10% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe collected organic was dried over magnesium sulfate
  5. filtrationfiltered
  6. washThe filtrate was passed through an Isolute® SCX-2 cartridge (eluting with dichloromethane, dichloromethane/methanol (1:1) and 2M ammonia in methanol)

Sources & evidence

ORD record
ord-11e7fb57622c445fa2009b43efdcc9a9
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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