Methylhydroxylamine → HCID 178482037, compound

HRID 643661Notes

Reaction equation

HRID 643661 reaction equation
ClC1C=C(NC2OC([C@@:14]3(C)[NH:19][C:18](=[NH:20])[N:17](C)C(=O)C3)=NN=2)C=CC=1.[CH3:24]NO.[CH3:27][CH2:28][O-:29].[Na+].[Br:31][C:32]1[CH:33]=C(C(=NC#N)C)[CH:35]=[CH:36][CH:37]=1>C(O)C>[Br:31][C:32]1[CH:33]=[C:27]([C:28]2([CH3:24])[O:29][N:19]([CH3:14])[C:18](=[NH:20])[NH:17]2)[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 11647MethylhydroxylamineHCID 2723922Sodium ethoxideHCID 10966114(1-(3-Bromophenyl)ethylidene)cyanamideHCID 178481314HCID 178481314, compound

Product 1

HCID 178482037HCID 178482037, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of the HCl salt of methylhydroxylamine (0.19 g, 2.2 mmol, 1 eq) in ethanol (25 mL) at 25° C. was added a 21% solution of NaOEt in ethanol (0.75 mL, 2.0 mmol, 0.9 eq) followed by (1-(3-bromophenyl) ethylidene) cyanamide (0.50 g, 2.2 mmol, 1 eq). After stirring at 25° C. for 10 min, the solvent was removed in vacuo. The residue was redissolved in CH2Cl2 (25 mL), the mixture was filtered, and the solvent was removed in vacuo to give 0.5 g (83%) of 5-(3-bromophenyl)-2,5-dimethyl-1,2,4-oxadiazolidin-3-imine (DB2, R1=Me, R4=Me) as a colorless oil: 1H NMR (CDCl3) δ 7.63 (t, J=1.8 Hz, 1H), 7.52. (dd, J=2.0, 1.1 Hz, 1H), 7.38 (dd, J=2.0, 1.1 Hz, 1H), 7.29 (t, J=7.9 Hz, 1H), 3.28 (s, 3H), 1.88 (s, 3H). MS (ESI) m/e 270.0, 272.0 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in CH2Cl2 (25 mL)
  3. filtrationthe mixture was filtered
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b31cedebed924a7da6632adce1fcf9ca
Source dataset
uspto-grants-2010_04
Patent number
US07700603B2

Reaction notes

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