2-Bromopropane → HCID 13645636, compound

HRID 280051Notes

Reaction equation

HRID 280051 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]([CH:17]([CH3:19])[CH3:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)(=[O:8])=[O:7].Cl[C:21]1[CH:22]=[C:23](S(Cl)(=O)=O)[CH:24]=[CH:25][C:26]=1Cl.OC[CH2:34][CH2:35][NH2:36].Br[CH:38](C)C.ClCl.[C:43]([O-:46])([O-])=O.[K+].[K+].[C:49]([O-:52])([O-])=O.[Cs+].[Cs+]>C1(C)C(C)=CC=CC=1.C(OCC)C>[CH3:49][O:52][C:21]1[CH:22]=[C:23]([CH2:34][CH2:35][N:36]([CH3:38])[CH2:2][CH2:3][CH2:4][N:5]([CH:17]([CH3:19])[CH3:18])[S:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)(=[O:8])=[O:7])[CH:24]=[CH:25][C:26]=1[O:46][CH3:43]

Participants

10

Reactant 7

HCID 63582-BromopropaneHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 90863-Amino-1-propanolHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 24526ChlorineHCID 23323135HCID 23323135, compound

Product 1

HCID 13645636HCID 13645636, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

N-(3-Chloropropyl)-N-isopropyl-3,4-dichlorobenzenesulfonamide, prepared by reacting 3,4-dichlorobenzenesulfonyl chloride with 3-hydroxypropylamine followed by N-alkylation with 2-bromopropane and displacement of the hydroxyl group by chlorine, (13.94 g), N--CH3 homoveratrylamine (8.23 g), K2CO3 (2.90 g) and Cs2CO3 (7.39 g) in xylene (300 mL) was heated and stirred for 5 days. The reaction was cooled, filtered and stripped to provide a partially solid crude product which was stirred with diethyl ether, filtered and the filtrate stripped to provide 17.11 g. This material was chromatographed on dry-column silica gel (500 g) using ethyl acetate to provide the product which was recrystallized from diethyl ether-hexane to give the impure product (3.95 g) (m.p. 62°-64° C.). A second recrystallization from diethyl ether-hexane provided pure product (3.57 g, m.p. 65°-66° C.).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto provide a partially solid crude product which
  5. filtrationfiltered
  6. customto provide 17.11 g
  7. customThis material was chromatographed on dry-column silica gel (500 g)
  8. customto provide the product which
  9. customwas recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-6067c16bed734e6aadb1642eded85e4b
Source dataset
uspto-grants-1986_05
Patent number
US04587360

Reaction notes

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