Dimethylformamide dimethyl acetal → HCID 68117268, compound

HRID 1657701Notes

Reaction equation

HRID 1657701 reaction equation
COC(OC)N(C)C.[N+:9]([C:12](=[C:16]1[NH:21][CH2:20][CH2:19][CH2:18][S:17]1)[C:13](=[O:15])C)([O-:11])=[O:10]>C(Cl)(Cl)Cl.CO.C(Cl)Cl>[N+:9]([C:12](=[C:16]1[NH:21][CH2:20][CH2:19][CH2:18][S:17]1)[CH:13]=[O:15])([O-:11])=[O:10]

Participants

6

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 714007471-Nitro-1-(1,3-thiazinan-2-ylidene)propan-2-one

Product 1

HCID 68117268HCID 68117268, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

5.95 g of N,N-dimethyl formamide dimethyl acetal in 25 ml of chloroform was added dropwise at room temperature to a mixture of 8.0 g of 2 b in 50 ml of chloroform and the mixture was stirred for one hour at room temperature, then was heated to reflux and stirred for 12.5 hours. The solvent then was evaporated under reduced pressure to give a mushy solid, which was passed through fluorosil, using methylene chloride, then methanol, as eluents. The resulting material then was passed through fluorosil using a 99:1 mixture of methylene chloride and methanol as eluent to give 21 as a yellow solid, m.p.: 171°-172°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. stirringstirred for 12.5 hours
  4. customThe solvent then was evaporated under reduced pressure
  5. customto give a mushy solid, which

Sources & evidence

ORD record
ord-4f4789c8eb0f461d8c5740e6f32d379e
Source dataset
uspto-grants-1976_06
Patent number
US03962225

Reaction notes

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