Benzaldehyde → HCID 59369679, compound

HRID 45376Notes

Reaction equation

HRID 45376 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>O1CCCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59369679HCID 59369679, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.20 g, 0.81 mmol), benzaldehyde (0.086 g, 0.81 mmol) and titanium(IV) isopropoxide (0.29 g, 1.01 mmol) in anhydrous tetrahydrofuran (2 mL) was stirred at ambient temperature for 18 h. Sodium cyanoborohydride (0.036 g, 0.57 mmol) was added to the mixture and stirring was continued at ambient temperature for another 6 h. The reaction was quenched with the addition of water (2 mL). The precipitate obtained was filtered and washed with ethanol. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to obtain the title compound as a white solid in 58% yield (0.16 g); m.p. 169-172° C.; 1H NMR (CDCl3, 300 MHz) δ 7.37-7.23 (m, 10H), 6.02 (s, 1H), 5.69 (s, 1H), 4.54 (d, J=5.6 Hz, 2H), 4.43 (s, 2H), 2.49 (s, 3H); MS (ES+) m/z 338.3 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued at ambient temperature for another 6 h
  3. customThe reaction was quenched with the addition of water (2 mL)
  4. customThe precipitate obtained
  5. filtrationwas filtered
  6. washwashed with ethanol
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ca6aa38e863d4b319296456fe36360de
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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