Dimethylformamide → HCID 14230767, compound

HRID 621055Notes

Reaction equation

HRID 621055 reaction equation
CN(C)C=O.[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[OH:37])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:44](Br)[CH:45]=[CH2:46]>O>[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[O:37][CH2:46][CH:45]=[CH2:44])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromide2×HCID 11430Potassium Carbonate2×HCID 13338941HCID 13338941, compound

Product 1

HCID 14230767HCID 14230767, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 70.5 ml of N,N-dimethylformamide are added 7.05 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate and 3.3 g of potassium carbonate. Then, under ice-cooling and stirring 2.12 g of allyl bromide is added dropwise over a period of 5 minutes. The mixture is further stirred under ice-cooling for 4 hours. To this reaction mixture are added 1.65 g of potassium carbonate and 1.06 g of allyl bromide, and the mixture is stirred for an additional 4 hours. The reaction mixture is diluted with 150 ml of water and extracted three times with 100 ml portions of ether. The ether extract is washed twice with 100 ml portios of aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)] and crystallized from ether-hexane to give 7.0 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-allyloxyiminoacetate, m.p. 115°- 116° C.

Workup

  1. temperatureThen, under ice-cooling
  2. additionis added dropwise over a period of 5 minutes
  3. temperaturecooling for 4 hours
  4. stirringthe mixture is stirred for an additional 4 hours
  5. extractionextracted three times with 100 ml portions of ether
  6. extractionThe ether extract
  7. washis washed twice with 100 ml portios of aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. customthe residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)]
  11. customcrystallized from ether-hexane

Sources & evidence

ORD record
ord-bf9b91fe3242484ea2ea2f988a552c7b
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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