Dichloromethane → HCID 178507228, compound

HRID 1197632Notes

Reaction equation

HRID 1197632 reaction equation
[C:1]12([C:11]3O[N:14]=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:16][NH2:17].ClCCl>>[C:1]12([C:11]3[CH:12]=[C:13]([NH2:14])[NH:17][N:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 11805799HCID 11805799, compound

Product 1

HCID 178507228HCID 178507228, compoundYield 96.3%

Procedure

A solution of 2.40 g (11.80 mmol) of 5-adamantylisoxazole and 1.18 g (23.60 mmol) of hydrazine hours. The solvent was removed in vacuo and the residue was taken up in 50 mol of dichloromethane. The solution was concentrated in vacuo to yield 2.47 g (96%) of a light brown oil. The crude material was purified by chromatography on silica gel to yield 200 g (78%) of a pale yellow solid: Rf 0.45 in 2/2/1 ligroin/CH2Cl2 /CH3OH; 1H NMR (CDCl3) δ 1.51 (S, 6H, the δ hydrogens of the adamantyl ring), 1.65 (S, 6H, the β hydrogens of the adamantyl ring, 1.81 (S, 3H, the three bridgehead protons), 5.16 (S, 1H, --C=CH--). All the analytical data are identical to those obtained from an authenticated sample.

Workup

  1. customThe solvent was removed in vacuo
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-99201c373cbc41b3b0cc748f257294ef
Source dataset
uspto-grants-1994_01
Patent number
US05276158

Reaction notes

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