Hydrazine hydrate (1:1) → 3-[[4-(4-chlorophenyl)-2-thiazolyl]methoxy]benzenemethanamine

HRID 349164Notes

Reaction equation

HRID 349164 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH2:21][N:22]4C(=O)C5=CC=CC=C5C4=O)[CH:18]=[CH:19][CH:20]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.O.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH2:21][NH2:22])[CH:18]=[CH:19][CH:20]=3)[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69412703HCID 69412703, compound2×

Product 1

HCID 102461073-[[4-(4-chlorophenyl)-2-thiazolyl]methoxy]benzenemethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The phthalimide compound (1.65 grams) (Scheme C, Compound C2) was suspended in ethanol (100 mL). Hydrazine hydrate (1 mL) was added and the reaction was stirred at reflux for 2 hours before being cooled to ambient temperature. The mix was then filtered and the filtrate was evaporated. The crude solid was dissolved in dichloromethane, then sequentially washed with 1 N potassium hydroxide and water. The organic layer was then evaporated to give 3-[[4-(4-chlorophenyl)-2-thiazolyl]methoxy]benzenemethanamine Compound 11. Mp 117–118.5° C.; MS 331 (MH+); 1HNMR (CDCl3) δ 7.85 (d, 2H), 7.50 (s, 1H), 7.40 (d, 2H), 5.43 (s, 2H), 3.86 (s, 2H).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe mix was then filtered
  3. customthe filtrate was evaporated
  4. dissolutionThe crude solid was dissolved in dichloromethane
  5. washsequentially washed with 1 N potassium hydroxide and water
  6. customThe organic layer was then evaporated

Sources & evidence

ORD record
ord-a352828d689c423fb0c3e5e559ab18f0
Source dataset
uspto-grants-2007_02
Patent number
US07179808B2

Reaction notes

Loading…