1-Chloro-2,4-Dinitrobenzene → HCID 178484976, compound

HRID 426679Notes

Reaction equation

HRID 426679 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[C:14]([NH:16][C:17]([NH:22][CH3:23])=[N:18][CH2:19][CH2:20][SH:21])#[N:15]>C(O)C>[C:14]([NH:16][C:17]([NH:22][CH3:23])=[N:18][CH2:19][CH2:20][S:21][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])#[N:15]

Participants

4

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 178485018HCID 178485018, compound

Product 1

HCID 178484976HCID 178484976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of cysteamine hydrochloride (5.68 g) in water (20 ml) was added to a suspension of N-cyano-N,S-dimethylisothiourea (6.46 g) in ethanol (100 ml). A solution of sodium hydroxide (4.0 g) in water (20 ml) was added to the mixture and the suspension was heated under reflux for one hour. The resulting clear solution was concentrated to remove ethanol, a little more water was added and the alkaline aqueous solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH4 with hydrochloric acid and extracted with ethyl acetate. This latter organic extract was dried and evaporated to give N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine (6.12 g) as a colourless oil. In order to characterise this product a solution of 2,4-dinitrochlorobenzene (7.7 g) in 95% ethanol (50 ml) was added to a solution of N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine (6.0 g) in 95% ethanol. The mixture was refluxed for one hour and cooled. The resulting crystalline solid (7.73 g) was collected and was triturated with a large volume of ether and was recrystallised from acetonitrile to afford N-cyano-N'-methyl-N"-[S-(2,4-dinitrophenyl)-2-mercaptoethyl]guanidine, m.p. 210°-211° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. temperaturecooled
  3. customThe resulting crystalline solid (7.73 g) was collected
  4. customwas triturated with a large volume of ether
  5. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-746236050c654b1199a5f59015708c70
Source dataset
uspto-grants-1979_10
Patent number
US04171325

Reaction notes

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