Hydrochloric Acid → HCID 90907901, compound

HRID 1881659Notes

Reaction equation

HRID 1881659 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-5066e54690cb431baf24144e7a3ed157
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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