2,6-Lutidine → HCID 135965018, compound

HRID 2049179Notes

Reaction equation

HRID 2049179 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([N:11]=[N:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:16]([O:28]CC)=[C:15](C(O)=O)[CH:14]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Br.[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH2:42].N1C(C)=CC=CC=1C>O1CCCC1>[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][S:2]([C:5]1[CH:6]=[C:7]([N:11]=[N:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:16]([OH:28])=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 20344648HCID 20344648, compoundHCID 450384506-Bromohexan-1-amine--hydrogen bromide (1/1)

Product 1

HCID 135965018HCID 135965018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-[3-chlorosulfonylphenylazo]-1-ethoxycarboxy-5-methanesulfonamidonaphthalene (20.4 g), 6-bromohexylamine hydrobromide (14.4 g), 2,6-lutidine (600 ml) and tetrahydrofuran (30 ml) was reacted for one hour at 50°-55° C. The mixture was cooled and filtered; the filtrate was concentrated to an oil which was dissolved in a minimum amount of acetonitrile and chromatographed on silica gel using acetonitrile as the eluant. The orange colored eluate was concentrated and cooled to obtain the product; yield 7.3 g (32%), m.p. 163°-5° C.

Workup

  1. customwas reacted for one hour at 50°-55° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to an oil which
  5. dissolutionwas dissolved in a minimum amount of acetonitrile
  6. customchromatographed on silica gel
  7. concentrationThe orange colored eluate was concentrated
  8. temperaturecooled
  9. customto obtain the product

Sources & evidence

ORD record
ord-b4a6d9de1155433387c4caf899e8f275
Source dataset
uspto-grants-1980_04
Patent number
US04197080

Reaction notes

Loading…