Ammonia → HCID 66956546, compound

HRID 2066675Notes

Reaction equation

HRID 2066675 reaction equation
[Br:1][C:2]1[N:3]([CH2:10][CH:11]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[CH2:12][O:13][Si](C(C)(C)C)(C)C)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.Cl.C(=O)=O.CC(C)=O.N>CCO.CO>[Br:1][C:2]1[N:3]([CH2:10][CH:11]([CH2:21][OH:22])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18522661Acetone cardiceHCID 66956501HCID 66956501, compound

Product 1

HCID 66956546HCID 66956546, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A suspension of silyl ether 178 (7.35 g, 14.5 mmol) in a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (150 mL) was stirred at room temperature for 4 h, and then kept at 4° C. for 12 h. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7M NH3 in MeOH (9.8 mL) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 33-75% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 75% EtOAc/petroleum ether and EtOAc gave 2-[(2-bromo-4-nitro-1H-imidazol-1-yl)methyl]-1,3-propanediol (179) (3.42, 85%) as a white solid: mp (MeOH/CH2Cl2/hexane) 110-112° C.; 1H NMR [(CD3)2SO] δ 8.50 (s, 1H), 4.65 (t, J=5.0 Hz, 2H), 4.07 (d, J=7.3 Hz, 2H), 3.41 (m, 4H), 2.06 (m, 1H). Anal. (C7H10BrN3O4) C, H, N.

Workup

  1. waitkept at 4° C. for 12 h
  2. stirringwith stirring
  3. concentrationconcentrated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 33-75% EtOAc/petroleum ether firstly gave foreruns
  6. washfurther elution with 75% EtOAc/petroleum ether and EtOAc

Sources & evidence

ORD record
ord-9cdc2f3557444dd9a10a5fb81f48903f
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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