Ammonia → 16459-44-2

HRID 459674

Reaction equation

HRID 459674 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.C[N:14](C)[CH:15]=[CH:16][C:17]#N.N>O.C(O)CC>[NH2:14][C:15]1[N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[N:11]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 974973-(Dimethylamino)prop-2-enenitrile2×HCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 1267877116459-44-2

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

7.65 g (50 mmol) of 4-nitrophenylhydrazine was suspended in 70 mL of water and 10 mL of n-propanol and the suspension was heated to about 50° C. At this temperature, 5 g (50 mmol) of concentrated hydrochloric acid and 4.81 g (50 mmol) of 3-dimethylaminoacrylonitrile were then added. After an additional 15 minutes, 3.8 mL (50 mmol) of a 25% ammonia solution was added dropwise within 15 minutes. The reaction mixture was then allowed to agitate at about 50° C. until the 3-dimethylaminoacrylonitrile had completely reacted (about 1 hour) after which the resulting dark-brown suspension was cooled in an ice bath. The precipitate was filtered off, washed 3 times with small portions of cold water and then dried. Yield of crude product: 9.4 g (46 mmol. 92% of the theoretical).

Workup

  1. customhad completely reacted (about 1 hour) after which the resulting dark-brown suspension
  2. temperaturewas cooled in an ice bath
  3. filtrationThe precipitate was filtered off
  4. washwashed 3 times with small portions of cold water
  5. customdried

Sources & evidence

ORD record
ord-6bac166120524a40b37f69db9f43e5ef
Source dataset
uspto-grants-2007_03
Patent number
US07195649B2

Linked notes

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