Hydrochloric Acid → HCID 86604761, compound

HRID 2103930Notes

Reaction equation

HRID 2103930 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[NH2:28])[C:5]([NH:7][N:8]=[C:9]([C:11]1[C:15]([OH:16])=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[S:13][CH:12]=1)[CH3:10])=[O:6].C[C:30](C)([O-:32])C.[Na+].Cl>O1CCCC1>[Cl:24][C:19]1[CH:18]=[C:17]([C:14]2[S:13][CH:12]=[C:11]([C:9](=[N:8][NH:7][C:5]([C:4]3[CH:25]=[CH:26][C:27]4[NH:28][C:30](=[O:32])[NH:1][C:2]=4[CH:3]=3)=[O:6])[CH3:10])[C:15]=2[OH:16])[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23676156Sodium t-butoxideHCID 72359952HCID 72359952, compound

Product 1

HCID 86604761HCID 86604761, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3,4-diamino-N′-[1-{5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl}ethylidene]-benzohydrazide (30 mg, 0.064 mmol, see the synthetic example 176) in tetrahydrofuran (3.0 mL) was added sodium tert-butoxide (12 mg, 0.13 mmol) and N,N′-carbonyl diimidazole (15 mg, 0.095 mmol). The reaction mixture turned clear orange and was stirred at room temperature for 16 hours, and then N,N′-carbonyl diimidazole (15 mg, 0.095 mmol) was added. The reaction mixture was stirred further for 12 hours, acidified with 1M aqueous HCl solution (0.7 mL) and concentrated under the reduced pressure. To the residue was added water (4 mL), then the precipitated solid was collected by filtration and dried by means of a vacuum pump to give the desired product as a pale yellow solid (yield 97%).

Workup

  1. stirringThe reaction mixture was stirred further for 12 hours
  2. concentrationconcentrated under the reduced pressure
  3. additionTo the residue was added water (4 mL)
  4. filtrationthe precipitated solid was collected by filtration
  5. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-51030e49a8ed4896a9918de5d7d067bb
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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