Hydrochloric Acid → HCID 70523952, compound

HRID 1164248Notes

Reaction equation

HRID 1164248 reaction equation
C(Cl)(Cl)Cl.[CH3:5][CH2:6][CH2:7][CH2:8][CH:9]([CH:23]1[CH2:28][C:27](=[O:29])[NH:26][C:24]1=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:30]1([C:36]2[NH:37][C:38]3[C:43]([C:44]=2[NH2:45])=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[N+:46]([C:49]1[CH:50]=[C:51]([S:55](Cl)(=[O:57])=[O:56])[CH:52]=[CH:53][CH:54]=1)([O-])=O.Cl>[Zn].O.CC(C)=O.N1C=CC=CC=1>[CH3:5][CH2:6][CH2:7][CH2:8][CH:9]([CH:23]1[CH2:28][C:27](=[O:29])[NH:26][C:24]1=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:30]1([C:36]2[NH:37][C:38]3[C:43]([C:44]=2[NH:45][S:55]([C:51]2[CH:52]=[CH:53][CH:54]=[C:49]([NH2:46])[CH:50]=2)(=[O:57])=[O:56])=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6212ChloroformHCID 84763-Nitrobenzenesulfonyl chlorideHCID 70524012HCID 70524012, compound

Product 1

HCID 70523952HCID 70523952, compoundYield 179%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalyst2×HCID 180AcetoneSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To 200 cc of a chloroform were added 22.28 g (0.04 mole) of 5-octadecyl succinimide-2-phenyl-3-aminoindole and 9.1 g (0.01 mole) of m-nitrobenzene sulfonic acid chloride, and to the mixture solution were dropwise added 3.24 g of pyridine under nitrogen gas flow, and stirred over a period of 4 hours, and the thus deposited Precipitate was filtered, whereby 18 g of crude crystals of 5-octadecyl succinimide-2-phenyl-3-{N-(3-nitrobenzene sulfonyl)amino}indole were obtained. 16 g of the obtained crystals were added to 140 ml of acetone, and to the solution were added 3.5 g of zinc powder and 7 ml of hydrochloric acid at a temperature of from 15° to 20° C. and, keeping the temperature, further added alternately 5.7 g of zinc powder and 15 ml of hydrochloric acid. This was stirred for 30 minutes after the addition and was added with stirring to 100 ml of water to deposit crystals. The crystals were centrifugally separated, stirred, washed, refined by column chromatography, and then dried, thereby obtaining 12.8 g of an objective product.

Workup

  1. filtrationthe thus deposited Precipitate was filtered
  2. customwhereby 18 g of crude crystals of 5-octadecyl succinimide-2-phenyl-3-{N-(3-nitrobenzene sulfonyl)amino}indole were obtained
  3. stirringThis was stirred for 30 minutes
  4. additionafter the addition
  5. additionwas added
  6. customThe crystals were centrifugally separated
  7. stirringstirred
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-701a717044a640d1a26b66a90df9af5b
Source dataset
uspto-grants-1983_01
Patent number
US04368260

Reaction notes

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