Pyridine → HCID 18327315, compound

HRID 1250173Notes

Reaction equation

HRID 1250173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[N:11][N:10]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]=1[NH2:21].N1C=CC=CC=1.[Cl:28][CH:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:30](Cl)=[O:31]>CN(C)C=O>[Cl:28][CH:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:30]([NH:21][C:9]1[N:10]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=[N:12][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 102902Chloro(phenyl)acetyl chlorideHCID 18327312HCID 18327312, compound

Product 1

HCID 18327315HCID 18327315, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.), stirred solution of 5-(2-fluorophenyl)-3-phenylsulfenylmethyl-3H-1,2,3-triazol-4-ylamine (1.30 g, 4.32 mmol) in dimethylformamide (30 ml) under nitrogen was added pyridine (0.46 ml, 5.62 mmol) followed by rac-α-chlorophenylacetyl chloride (0.79 ml, 4.97 mmol). The reaction mixture was stirred at 0° C. for 1 hour and subsequently poured into distilled water (200 ml). The aqueous solution was extracted with ethyl acetate (2×100 ml) and the combined organic extracts were washed with citric acid (100 ml, 10% aqueous), sodium hydrogencarbonate (100 ml, sat. aqueous), water (100 ml), brine (100 ml) and dried (Na2SO4). The solvent was removed in vacuo and the resulting oil was crystallised from hot diethyl ether to afford 2-chloro-N-[5-(2-fluoro-phenyl)-3-phenylsulfenylmethyl-3H-1,2,3-triazol-4-yl]-2-phenylacetamide (1.514 g, 78%) as a pale solid. δH (400 MHz, CDCl3) 5.37 (1H, s, CHCl), 5.49 (1 H, d, J=14.4, PhSCH2A), 5.61 (1H, d, J=14.4, PhSCH2B), 7.11 (1H, dd, J=11 and 8.6, ArH), 7.24-7.44 (12H, m, ArH), 7.82 (1H, td, J=7.6 and 1.4, ArH), 8.21-8.19 (1H, m, NH); m/z (ES+) 453 (35 ClM+H+) and 455 (37 ClM+H+).

Workup

  1. additionsubsequently poured
  2. distillationinto distilled water (200 ml)
  3. extractionThe aqueous solution was extracted with ethyl acetate (2×100 ml)
  4. washthe combined organic extracts were washed with citric acid (100 ml, 10% aqueous), sodium hydrogencarbonate (100 ml, sat. aqueous), water (100 ml), brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe resulting oil was crystallised from hot diethyl ether

Sources & evidence

ORD record
ord-c1ff2c76826848fc964cea3548fa7079
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

Loading…