Dimethylformamide → HCID 86625104, compound

HRID 1042622Notes

Reaction equation

HRID 1042622 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:41][C:42](=[O:68])/[CH:43]=[CH:44]/[C:45]2[CH:50]=[CH:49][C:48]([O:51][C:52](=[O:67])[C:53]3[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][CH2:62][C:63]([F:66])([F:65])[F:64])=[CH:55][CH:54]=3)=[CH:47][CH:46]=2)[C:11]([C:14](=[O:40])/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:39])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)([OH:13])[OH:12])=[CH:6][CH:5]=1)([O-])=O.CCCCCC.C[N:76](C)C=O>O.[Zn]>[NH2:76][C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[CH:6][C:7]=1[CH:10]([CH2:41][C:42](=[O:68])/[CH:43]=[CH:44]/[C:45]1[CH:50]=[CH:49][C:48]([O:51][C:52](=[O:67])[C:53]2[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][CH2:62][C:63]([F:66])([F:65])[F:64])=[CH:55][CH:54]=2)=[CH:47][CH:46]=1)[C:11]([C:14](=[O:40])/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:39])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)([OH:13])[OH:12]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8058HexaneHCID 86625105HCID 86625105, compound

Product 1

HCID 86625104HCID 86625104, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

7.60 g (7.64 mmol) of 2-(4-nitrophenyl)-1,3di[(2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl]propanediol are dissolved in a mixture of 45 ml of N,N-dimethylformamide and 5 ml water. 12.39 g (45.84 mmol) ferric chloride hexahydrate are added. 4.99 g (76.4 mmol) Zinc powder are added portionwise within 40 min. The mixture is allowed to react for 2 hours. The reaction mixture is then partitioned between ethyl acetate and water and filtered. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 1000 g silica gel using toluene:ethyl acetate 1:1 as eluant and crystallization form ethylacetate:hexane mixture to yield 4.30 g of 2-(2,4-Diaminophenyl)-1,3di[(2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl]propanediol.

Workup

  1. customto react for 2 hours
  2. customThe reaction mixture is then partitioned between ethyl acetate and water
  3. filtrationfiltered
  4. washThe organic phase is washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customcrystallization
  9. customform ethylacetate

Sources & evidence

ORD record
ord-0165d524945f46fda8c54f19f2f81bc7
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

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