Hydrochloric Acid → HCID 90907901, compound

HRID 2103932Notes

Reaction equation

HRID 2103932 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].CC(C)([O-])C.[Na+].C1N=CN([C:40](N2C=NC=C2)=[S:41])C=1.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:40](=[S:41])[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 23676156Sodium t-butoxideHCID 72359952HCID 72359952, compound

Product 1

HCID 90907901HCID 90907901, compoundYield 52%

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′-thiocarbonyldiimidazole (23 mg, 0.13 mmol). The reaction mixture turned clear orange and was stirred at room temperature for 16 hours, and then was acidified with 1M aqueous HCl solution (1.0 mL) and concentrated under the reduced pressure. The precipitated solid was collected by filtration, washed with chloroform, washed with methanol and dried by means of a vacuum pump to give the desired product as a pale brown solid (yield 52%).

Workup

  1. concentrationconcentrated under the reduced pressure
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with chloroform
  4. washwashed with methanol
  5. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-2a9b9c67e919425a87cd873050e71742
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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