Hydroxylamine → HCID 19017868, compound

HRID 1728362Notes

Reaction equation

HRID 1728362 reaction equation
[NH2:1][OH:2].C[Si](N=[C:8]=[O:9])(C)C.[NH4+:10].[Cl-].[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1>>[OH:2][N:1]([CH2:14][CH:13]1[CH2:14][CH2:13][CH2:12][CH2:16][CH2:16][CH2:12]1)[C:8]([NH2:10])=[O:9]

Participants

5

Reactant 4

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanate

Product 1

HCID 19017868HCID 19017868, compound

Procedure

To a solution of hydroxylamine (3.0 g, 20.9 mmol) from above, in THF (25 mL) was added trimethylsilylisocyanate (2.9 g, 25.2 mmol) and the reaction was stirred for 30 min. The reaction was treated with saturated aqueous NH4Cl and the aqueous mixture extracted with ethyl acetate (4×120 mL). The organics were combined, dried over MgSO4 then concentrated in vacuo. The resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 50:50) followed by crystallization in ethyl acetate/hexanes to afford N-hydroxy-N-1-(1-cycloheptyl)methylurea. m.p.=110°-112° C.; 1H NMR (300 MHz, DMSO-d6): δ1.09 (m, 2H), 1.2-1.7 (m, 10H), 1.79 (m, 1H), 3.14 (d, 2H, J=7.4), 6.16 (bs, 2H), 9.17 (s, 1H); Analysis calc'd for C9H18N2O2 : C, 58.04, H, 9.74, N, 15.04; Found: C, 57.85 , H, 9.60, N, 15.10.

Workup

  1. extractionthe aqueous mixture extracted with ethyl acetate (4×120 mL)
  2. dry with materialdried over MgSO4
  3. concentrationthen concentrated in vacuo
  4. customThe resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 50:50)
  5. customfollowed by crystallization in ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0b7a0b3c68fb4376b510647f1e03a6a4
Source dataset
uspto-grants-1994_07
Patent number
US05326787

Reaction notes

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