Triethylamine → HCID 12803104, compound

HRID 1904775Notes

Reaction equation

HRID 1904775 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C:19]#[N:20].C(N(CC)CC)C>CN(C)C=O.O>[C:19]([CH2:18][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([NH:8][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])[CH:10]=2)[NH:14][CH:13]=1)#[N:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 12803100HCID 12803100, compound

Product 1

HCID 12803104HCID 12803104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Dimethyl sulphamoyl chloride (1.2 ml) was added dropwise to a stirred solution 5-amino-1H-indole-3-acetonitrile (1.7 g) in dry dimethyl-formamide (50 ml) containing triethylamine (2.8 ml). After 3 h, the resulting suspension was diluted with water (20 ml) and stirred for 30min. The resulting solution was poured into water (100 ml) and extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with water (100 ml) and brine (2×100 ml), dried (Na2SO4) and evaporated in vacuo, to give a dark brown oil which was purified by column chromatography (Kieselgel 60, 100 g) eluted with ether/ethyl acetate, (9:1) to give the title compound as white solid (0.75 g) m.p. 147°-150°.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined organic extracts were washed with water (100 ml) and brine (2×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give a dark brown oil which
  6. customwas purified by column chromatography (Kieselgel 60, 100 g)
  7. washeluted with ether/ethyl acetate, (9:1)

Sources & evidence

ORD record
ord-a79139f551bd46f7bfcb05ad53c3e4b1
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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