Triethylamine → 4-[N-(3-isopropylaminopropyl)sulphamoyl]aniline

HRID 1071940Notes

Reaction equation

HRID 1071940 reaction equation
[S:1](F)(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].[CH:12]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])([CH3:14])[CH3:13].C(N(CC)CC)C>>[CH:12]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][S:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)(=[O:10])=[O:2])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 668234-Aminobenzenesulfonyl fluorideHCID 76888N-Isopropylpropane-1,3-diamine

Product 1

HCID 223905954-[N-(3-isopropylaminopropyl)sulphamoyl]aniline

Procedure

Sulphanilyl fluoride (6.5 g, 37.1 mmol), N-isopropyl-1,3-propanediamine (5.71 ml, 40.8 mmol) and triethylamine (5.69 ml, 40.8 mmol) in N-butanol (15 ml) was heated at reflux for 10 hours. The mixture was allowed to cool, silica was added and the volatiles were evaporated. The residue was purified by chromatography eluting with DCM/methanolic ammonia (100:0) increasing in polarity to (90:10) to give the title compound as a clear oil which crystallized on standing (8.81 g, 88%). NMR: 0.89 (d, 6H), 1.43 (m, 2H), 2.41 (t, 2H), 2.58 (m, 1H), 2.68 (t, 2H), 3.16 (s, 2H), 5.85 (s, 2H), 6.58 (d, 2H), 7.38 (d, 2H); m/z: 272.

Workup

  1. temperatureat reflux for 10 hours
  2. temperatureto cool
  3. additionsilica was added
  4. customthe volatiles were evaporated
  5. customThe residue was purified by chromatography
  6. washeluting with DCM/methanolic ammonia (100:0)
  7. temperatureincreasing in polarity to (90:10)

Sources & evidence

ORD record
ord-4c7914dbdc57425f85c0873291a050e9
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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