Sodium Bicarbonate → 5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-ylamine

HRID 556032Notes

Reaction equation

HRID 556032 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 579916495-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-ylamineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 50 ml eggplant-shaped flask were added 0.50 g (1.69 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 15 ml dichloromethane, and then added dropwise 2.9 ml (5.06 mmol) of 1.76 M BBR3 solution in dichloromethane. The resulting mixture was stirred at room temperature for 2 hours, the resultant was poured into 20 ml of a saturated aqueous sodium bicarbonate solution, a solid was precipitated, filtered, washed with water, and dried to obtain a crude product, which was subjected to a silica gel column chromatography eluted with petroleum ether/ethyl acetate (3:2) to obtain a 0.46 g product as a white solid in a yield of 95.8%, mp: 170-172□. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.02 (2H, s, CH2), 6.74˜6.76 (4H, m, 2ArH+NH2), 7.15˜7.40 (7H, m, ArH), 9.49 (1H, s, OH); EI-MS m/e (%): 282.0 (M+, 100), 205.0 (37); HREI-MS Calcd. for C16H14N2OS: 282.0827. found: 282.0824.

Workup

  1. customa solid was precipitated
  2. filtrationfiltered
  3. washwashed with water
  4. customdried
  5. customto obtain a crude product, which
  6. washeluted with petroleum ether/ethyl acetate (3:2)

Sources & evidence

ORD record
ord-aa710078901f4ae2b528323008a9162c
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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