Propylene Glycol → HCID 21427097, compound

HRID 437794Notes

Reaction equation

HRID 437794 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([OH:23])[CH:20](O)[CH3:21].CC1C=CC(S(O)(=O)=O)=CC=1.[OH-].[NH4+]>CC1C=CC=CC=1.C(O)CCC>[CH3:21][CH:20]1[CH2:19][O:23][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:16]([O-:18])=[O:17])[CH:4]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9]1

Participants

7

Reactant 4

HCID 1030Propylene GlycolHCID 6101p-Toluenesulfonic acidHCID 14923Ammonium HydroxideHCID 5969704-Amino-3-nitrobenzophenone

Product 1

HCID 21427097HCID 21427097, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 31.5 parts of (4-amino-3-nitrophenyl)phenylmethanone, 15.2 parts of 1,2-propanediol and 5 parts of 4-methylbenzenesulfonic acid in 40 parts of butanol and 450 parts of methylbenzene is stirred and refluxed for 17 hours. The reaction mixture is cooled and 90 parts of ammonium hydroxide are added (to remove the 4-methylbenzenesulfonic acid). The organic phase is separated, washed with water, dried, filtered and evaporated. The residue is crystallized from methylbenzene. The product is filtered off (the filtrate is set aside), yielding a first fraction of 13.8 parts of 4-(4-methyl-2-phenyl-1,3-dioxolan-2-yl)-2-nitrobenzenamine; mp. 155.2° C. The filtrate, which was set aside, is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane, methanol and hexane (88:2:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding a second fraction of 3.6 parts of 4-(4-methyl-2-phenyl-1,3-dioxolan-2-yl)-2-nitrobenzenamine.

Workup

  1. temperaturerefluxed for 17 hours
  2. temperatureThe reaction mixture is cooled
  3. customto remove the 4-methylbenzenesulfonic acid)
  4. customThe organic phase is separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from methylbenzene
  10. filtrationThe product is filtered off (the filtrate

Sources & evidence

ORD record
ord-6f6518b25fc7476b96d6644b3a747e35
Source dataset
uspto-grants-1977_06
Patent number
US04032536

Reaction notes

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