Hydrochloric Acid → HCID 13059650, compound

HRID 1164279Notes

Reaction equation

HRID 1164279 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([Cl:12])[C:4]=1[N:13]=[CH:14][N:15]([CH3:17])[CH3:16]>>[NH2:9][C:7]1[CH:6]=[C:5]([Cl:12])[C:4]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])=[C:3]([Cl:2])[CH:8]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13059649HCID 13059649, compound

Product 1

HCID 13059650HCID 13059650, compound

Conditions

Temperature
10 °C

Procedure

A 540 g. amount of stannous chloride is dissolved in 450 ml. of concentrated hydrochloric acid with stirring. The solution is cooled to 10° C. in an ice bath and 155 g. of N'-(2,6-dichloro-4-nitrophenyl)-N,N-dimethylformamidine (prepared as described above) is added portionwise, with stirring, at a rate to maintain the reaction temperature at 75° C. The reaction mixture is allowed to stand at room temperature for 18 hours, then is filtered. The filter cake is suspended in 200 ml. of ice water and concentrated sodium hydroxide is added until the reaction mixture is alkaline. The reaction mixture is filtered and the insolubles are collected and extracted with chloroform. The chloroform extracts are evaporated in vacuo to yield 102 g. of the product of the Example as pale yellow crystals, m.p. 121°-126° C.

Workup

  1. temperatureto maintain the reaction temperature at 75° C
  2. filtrationis filtered
  3. additionof ice water and concentrated sodium hydroxide is added until the reaction mixture
  4. filtrationThe reaction mixture is filtered
  5. customthe insolubles are collected
  6. extractionextracted with chloroform
  7. customThe chloroform extracts are evaporated in vacuo
  8. customto yield 102 g

Sources & evidence

ORD record
ord-d513689df32e4190b77234ec493a975f
Source dataset
uspto-grants-1983_01
Patent number
US04368335

Reaction notes

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