Cyclopentylamine → N-(Cyclopentylaminocarbonyl)-2,3-dichlorobenzenesulfonamide

HRID 236519Notes

Reaction equation

HRID 236519 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]=[C:13]=[O:14])(=[O:11])=[O:10].[CH:15]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16]1>C(#N)C>[CH:15]1([NH:20][C:13]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])(=[O:10])=[O:11])=[O:14])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 138527082,3-Dichlorobenzenesulfonyl isocyanate

Product 1

HCID 13852709N-(Cyclopentylaminocarbonyl)-2,3-dichlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 20 mL of the acetonitrile solution containing 2,3-dichlorobenzenesulfonyl isocyanate, prepared as described in the previous example, was added 2.5 mL of cyclopentylamine. This mixture was allowed to sit overnight. The solid precipitate was filtered off and triturated with 5 mL of acetonitrile. Filtration and drying afforded 5.0 g of the title compound as an off-white solid, m.p. 202°-207° C.; NMR (DMSO-d6): δ1.1-1.8 (m, 8H), 3.7 (m, 1H), 6.5 (br d, 1H), 7.6 (t, 1H), 7.9 (dd, 1H), 8.0 (dd, 1H), 10.8 (br s, 1H); IR (nujol): 3343, 1660, 1375, 1170 cm-1.

Workup

  1. customprepared
  2. filtrationThe solid precipitate was filtered off
  3. customtriturated with 5 mL of acetonitrile
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-06e6ed168fd14655bebf3edf8d5d11c7
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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