N,N-Dimethyl-1,3-propanediamine → HCID 21506083, compound

HRID 918634Notes

Reaction equation

HRID 918634 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][NH2:23]>O>[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][NH:23][C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 21506083HCID 21506083, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (22.4 g) in water (24 ml), 3-dimethylaminopropylamine (120 ml) was added, while cooling. Then the reaction mixture was heated to 100°C and kept at this temperature for 2 hours. After cooling and evaporating in vacuo to dryness, the residue was dissolved in water (80 ml) and adjusted to a pH of 7.5 by addition of 4N hydrochloric acid. The precipitated 4-(3-dimethylaminopropylamino)-3-nitro-5-sulphamyl-benzoic acid was collected by suction and recrystallized from water. The melting point was 262°C (decomp.).

Workup

  1. additionwas added
  2. temperaturewhile cooling
  3. temperatureAfter cooling
  4. customevaporating in vacuo to dryness
  5. dissolutionthe residue was dissolved in water (80 ml)
  6. additionadjusted to a pH of 7.5 by addition of 4N hydrochloric acid
  7. customThe precipitated 4-(3-dimethylaminopropylamino)-3-nitro-5-sulphamyl-benzoic acid was collected by suction
  8. customrecrystallized from water

Sources & evidence

ORD record
ord-a828cb37884f428f868e9189bbf05889
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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