Succinimide → HCID 9942759, compound

HRID 2287329Notes

Reaction equation

HRID 2287329 reaction equation
[CH2:1]([C:3]1[C:4]([NH2:13])=[C:5]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[Cl:14]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1.[K+].[Br-]>C(#N)C.C(OCC)(=O)C>[Cl:14][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]([NH2:13])=[C:5]([S:9]([NH2:12])(=[O:10])=[O:11])[CH:6]=1

Participants

7

Reactant 4

HCID 11439SuccinimideHCID 31398Chlorosuccinimide2×HCID 253877Potassium BromideHCID 187047302-Amino-3-ethylbenzene-1-sulfonamide

Product 1

HCID 9942759HCID 9942759, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-ethyl-2-aminobenzenesulfonamide (0.5043 g, 2.52 mmol) in 10 mL acetonitrile was added N-chlorosuccinimide (0.3163 g, 2.37 mmol). The mixture was stirred at reflux for 1 2.5 h, cooled, filtered, and concentrated in vacuo. Reaction was incomplete by 1H NMR; the purple solids were redissolved in acetonitrile and additional NCS (0.1019 g, 0.76 mmol) was added. The mixture was refluxed for 1 5 minutes and worked up as before. Column chromatography on the mixture of succinimide and D (40% ethyl acetate:hexanes) gave pure D (0.5224 g, 94%), m.p. 134-135° C. 1H NMR (300 MHz, DMSO): δ7.45 (3H, s), 7.19 (1H, d, J=2.1 Hz), 5.76 (2H, s), 2.53 (2H, q, J=7.3 Hz), 1.14 (3H, i, J=7.3 HZ). 13C NMR (300 MHz, DMSO): δ141.9, 131.8, 131.2, 125.4, 124.8, 118.1, 23.4, 12.7. FT-IR (KBr): 3457.8, 3427.9, 3358.4, 3268.9, 3080.1, 2970.8, 2364.5, 2334.7, 1630.6. 1556.1, 1541.2. 1451.7. 1312.6. 1188.3, 1148.6, 905.1, 875.3, 762.2, 611.3 cm-1. HRMS: M+ calculated=234.0230, found=234.0227.

Workup

  1. temperatureat reflux for 1 2.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customReaction
  6. temperatureThe mixture was refluxed for 1 5 minutes
  7. customgave pure D (0.5224 g, 94%), m.p. 134-135° C

Sources & evidence

ORD record
ord-bae7bce74206479bba9a953022279b64
Source dataset
uspto-grants-2000_07
Patent number
US06083947

Reaction notes

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