Dimethylformamide → HCID 178478846, compound

HRID 1262641Notes

Reaction equation

HRID 1262641 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15]([NH2:17])=N)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[ClH:18].[NH2:19][OH:20].C(=O)([O-])[O-].[Na+].[Na+].C[N:28](C)C=O>>[ClH:18].[ClH:18].[NH2:28][N:17]=[CH:15][NH:14][C:11]1[S:12][CH:13]=[C:9]([C:5]2[CH:4]=[C:3]([C:1](=[NH:2])[NH:19][OH:20])[CH:8]=[CH:7][CH:6]=2)[N:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 178509705HCID 178509705, compound

Product 1

HCID 178478846HCID 178478846, compound

Procedure

A stirred mixture of 3.4 g. (0.01 mole) of [4-(3-cyanophenyl)-2-thiazolyl]guanidine of Example 3, 1.38 g. (0.02 mole) of hydroxylamine hydrochloride and 4.24 g. (0.04 mole) of sodium carbonate in 60 ml. of dry N,N-dimethylformamide is heated under reflux for 6 hours. The mixture is filtered and the filtrate is diluted with a little water. The precipitate which forms is collected and is recrystallized from N,N-dimethylformamide. This solid is added to 150 ml. of a saturated ethanolic hydrochloric acid solution and the mixture is quickly filtered. The filtrate is cooled in ice to precipitate 0.4 g. of product, m.p. 246° (dec.).

Workup

  1. additionA stirred mixture of 3.4 g
  2. temperatureunder reflux for 6 hours
  3. filtrationThe mixture is filtered
  4. additionthe filtrate is diluted with a little water
  5. customThe precipitate which forms is collected
  6. customis recrystallized from N,N-dimethylformamide
  7. additionThis solid is added to 150 ml
  8. filtrationof a saturated ethanolic hydrochloric acid solution and the mixture is quickly filtered
  9. temperatureThe filtrate is cooled in ice
  10. customto precipitate 0.4 g

Sources & evidence

ORD record
ord-26ccb08a6de94c7f9c5e0f8fee031bd0
Source dataset
uspto-grants-1984_06
Patent number
US04452985

Reaction notes

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