Methanol → HCID 14390900, compound

HRID 2292344Notes

Reaction equation

HRID 2292344 reaction equation
CN([Si](C)(C)C)C(=O)C(F)(F)F.FC(F)(F)C(O)=O.[NH2:20][C:21]1[CH:22]=[C:23]([OH:28])[C:24](=[CH:26][CH:27]=1)[OH:25].Cl[C:30]([NH:32][NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])=[O:31].CO>C(#N)C.ClCCl.CCOCC>[OH:28][C:23]1[CH:22]=[C:21]([NH:20][C:30]([NH:32][NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])=[O:31])[CH:27]=[CH:26][C:24]=1[OH:25]

Participants

8

Reactant 4

HCID 887MethanolHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 21277172HCID 21277172, compoundHCID 21681927Phenylmethyl 2-(chlorocarbonyl)hydrazinecarboxylate

Product 1

HCID 14390900HCID 14390900, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

15.64 ml (80.0 mmol) of N-methyl-N-trimethylsilyltrifluoroacetamide was added to a suspension of 4.80 g (20.0 mmol) of 4-aminocatechol trifluoroacetate in 80 ml of dry acetonitrile. After stirring for 30 minutes, the dark solution was evaporated in vacuo and the dark residue was redissolved in 25 ml of dichloromethane. A solution of 4.56 g (20.0 mmol) of 2-(chlorocarbonyl)hydrazinecarboxylic acid, phenylmethyl ester in 50 ml of dichloromethane was slowly dropped in with stirring at 10° C. (40 minutes), and stirring was continued for 2 hours at room temperature. After evaporation in vacuo, the residue was taken up in a few ml of methanol and stirred until it became crystalline. The suspension was dluted with ether, and the precipitate was collected by suction; yield: 6.09 g, melting point 204° C., dec.

Workup

  1. customthe dark solution was evaporated in vacuo
  2. dissolutionthe dark residue was redissolved in 25 ml of dichloromethane
  3. stirringwith stirring at 10° C. (40 minutes)
  4. stirringstirring
  5. waitwas continued for 2 hours at room temperature
  6. customAfter evaporation in vacuo
  7. stirringstirred until it
  8. customthe precipitate was collected by suction

Sources & evidence

ORD record
ord-6a8d4420ff5f4659a7a166e260f9cc95
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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