Sodium Hydroxide → HCID 22492909, compound

HRID 1816341Notes

Reaction equation

HRID 1816341 reaction equation
[I:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:34].[OH-].[Na+]>N1C=CC=CC=1.O>[I:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]2[S:34][C:10]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([CH:23]5[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]5)[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 22493007HCID 22493007, compound

Product 1

HCID 22492909HCID 22492909, compoundYield 119.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of N′-(4-iodobenzoyl)-4-[4-(4-methylcyclohexyl)-1-piperazinyl]benzohydrazide (22.95 g) in pyridine (459 ml) was treated with phosphorus pentasulfide (11.2 g) and stirred at 120° C. for 2.5 hours. The reaction mixture was added a solution of sodium hydroxide (510 g) in water (9200 ml). The resulting precipitate was collected, washed with acetone. The powder was recrystallized from THF (800 ml) and dried to give 1-[4-[5-(4-iodophenyl)-1,3,4-thiadiazol-2-yl]phenyl]-4-(4-methylcyclohexyl)piperazine (16.42 g).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with acetone
  3. customThe powder was recrystallized from THF (800 ml)
  4. customdried

Sources & evidence

ORD record
ord-752017b266af4578b4c9fd5610b360c5
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

Loading…