Hydrochloric Acid → HCID 54532366, compound

HRID 1884409Notes

Reaction equation

HRID 1884409 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].[CH3:14]N(C(N(C)C)N(C)C)C.Cl.[NH2:25][NH:26][C:27]([NH2:29])=[O:28].Cl>CN(C=O)C.O>[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH2:12][CH:14]=[N:25][NH:26][C:27]([NH2:29])=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11236Semicarbazide hydrochlorideHCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 22225799N,N,2-trimethyl-3-nitroaniline

Product 1

HCID 54532366HCID 54532366, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
115 °C

Procedure

To a stirred solution of N,N-dimethyl-2-methyl-3-nitroaniline (5.40 g, 30 mmol) in dry DMF (30 ml) was added tris(dimethylamino)methane (6.54 g, 45 mmol) and the mixture was heated to 115° C. under N2 for 4 h. The progress of the reaction was monitored by TLC [EtOAc-hexanes (1:3)]. The dark red solution was cooled in an ice bath, diluted with DMF (20 ml) and a solution of semicarbazide hydrochloride (3.51 g, 31.5 mmol) and conc. HCl (5.4 ml) in water (50 ml) was added. Stirring was continued for 30 min and the pH was raised to 5.0 and after stirring at 0° C. for 30 min, the pH was further raised to 7.5. The precipitated yellow solid was filtered, washed with ice-cold water and ether and dried under vacuum. Recrystallisation from aq. EtOH afforded 31 as yellow microcrystals (3.93 g, 49%), mp 156-157° C. (Found: C, 49.65; H, 5.70; N. 26.14. C11H15N5O3 requires C, 49.81; H, 5.70; N, 26.39%); νmax (Nujol)/cm−1 3450, 3160, 1720, 1600, 1525, 1350.

Workup

  1. temperatureThe dark red solution was cooled in an ice bath
  2. temperaturethe pH was raised to 5.0
  3. stirringafter stirring at 0° C. for 30 min
  4. temperaturethe pH was further raised to 7.5
  5. filtrationThe precipitated yellow solid was filtered
  6. washwashed with ice-cold water and ether
  7. customdried under vacuum
  8. customRecrystallisation from aq. EtOH

Sources & evidence

ORD record
ord-67b7571032f84be9b4b7ba83b7926e7e
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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