N-methyl-N-(trimethylsilyl)trifluoroacetamide → HCID 56974509, compound

HRID 2292348Notes

Reaction equation

HRID 2292348 reaction equation
CN([Si](C)(C)C)C(=O)C(F)(F)F.[OH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[OH:24])[C:17]([NH:19][NH2:20])=[O:18].[C:25]1([CH2:31][O:32][C:33]([NH:35][NH:36][C:37](Cl)=[O:38])=[O:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:25]1([CH2:31][O:32][C:33]([NH:35][NH:36][C:37]([NH:20][NH:19][C:17](=[O:18])[C:16]2[CH:21]=[CH:22][C:23]([OH:24])=[C:14]([OH:13])[CH:15]=2)=[O:38])=[O:34])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 5863003,4-DihydroxybenzohydrazideHCID 21681927Phenylmethyl 2-(chlorocarbonyl)hydrazinecarboxylate

Product 1

HCID 56974509HCID 56974509, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.52 ml (0.10 mol) of N-methyl-N-trimethylsilyltrifluoroacetamide was added to a suspension of 4.20 g (0.025 mol) of 3,4-dihydroxybenzoic acid, hydrazide in 25 ml of dry acetonitrile. Stirring was continued at room temperature until a clear solution was formed (40 minutes). After evaporation in vacuo at 30°-40° C., the residue was dissolved in 25 ml of dry dichloromethane. This solution was dropped into a stirred suspension of 5.72 g (25.0 mmol) of [[[(phenylmethoxy)carbonyl]hydrazino]carbonyl]chloride at 5° C. After stirring for 1 hour at 0° C., the mixture was evaporated in vacuo and the oily residue was stirred with ether containing 4 ml of methanol until it became crystalline; yield after washing with ether and drying in vacuo: 8.77 g.

Workup

  1. customwas continued at room temperature until a clear solution
  2. customwas formed (40 minutes)
  3. customAfter evaporation in vacuo at 30°-40° C.
  4. dissolutionthe residue was dissolved in 25 ml of dry dichloromethane
  5. stirringAfter stirring for 1 hour at 0° C.
  6. customthe mixture was evaporated in vacuo
  7. stirringthe oily residue was stirred with ether containing 4 ml of methanol until it
  8. customyield
  9. washafter washing with ether
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-b84e99adb2f94653bc0752ecb32eec84
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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