N-Methylbenzeneethanamine → HCID 67408155, compound

HRID 913240Notes

Reaction equation

HRID 913240 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[CH3:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH3:12][N:13]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 11503N-MethylbenzeneethanamineHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 67408155HCID 67408155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 2-bromo-1,3-thiazole-5-carboxylate (0.5 g, 2.1 mmol) in THF (2 mL) was added N-methylphenethylamine (0.86 g, 6.4 mmol). The reaction was heated to 100° C. via microwave for 30 minutes. The reaction was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated. Purification by flash chromatography (15-50% ethyl acetate/hexanes) gave ethyl 2-[methyl(2-phenylethyl)amino]-1,3-thiazole-5-carboxylate. 1H NMR (600 MHz, DMSO-d6) δ 7.81 (s, 1H), 7.22 (m, 5H), 4.17 (q, J=7.34 Hz, 2H), 3.70 (t, J=7.33 Hz, 2H), 3.00 (s, 3H), 2.87 (t, J=7.63 Hz, 2H), 1.21 (t, J=7.01 Hz, 3H); ESIMS calcd 291.1 (M++H), found 291.0 (M++F).

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (15-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dbf77ea3c4d345e8a9c63ddb81012298
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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