Ammonium Chloride → HCID 19707509, compound

HRID 726749Notes

Reaction equation

HRID 726749 reaction equation
[C:1]([CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1)[CH2:4][NH2:5])#[N:2].C[Si]([N:24]=[C:25]=[O:26])(C)C.[Cl-].[NH4+]>O1CCCC1>[C:1]([CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH:7]=1)[CH2:4][NH:5][C:25]([NH2:24])=[O:26])#[N:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 19707500HCID 19707500, compound

Product 1

HCID 19707509HCID 19707509, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-cyano-2-(3-cyclopentyloxy-4-methoxyphenyl)ethylamine [3-amino-2-(3-cyclopentyloxy-4-methoxyphenyl)propionitrile, 0.17 g, 0.66 mmol] in tetrahydrofuran (5 mL) under an argon atmosphere was added trimethylsilyl isocyanate (0.13 mL, 0.96 mmol). The resulting mixture was stirred overnight at room temperature. Aqueous ammonium chloride was added, the mixture was extracted three times with 5% methanol/methylene chloride, the extract was dried (potassium carbonate) and evaporated. Purification of the residue by flash chromatography, eluting with 4% methanol/methylene chloride, provided the urea as a white solid: m.p. 55°-61° C. (sublimes).

Workup

  1. extractionthe mixture was extracted three times with 5% methanol/methylene chloride
  2. dry with materialthe extract was dried (potassium carbonate)
  3. customevaporated
  4. customPurification of the residue by flash chromatography
  5. washeluting with 4% methanol/methylene chloride

Sources & evidence

ORD record
ord-c7e2e59e291441c1a3da908915296541
Source dataset
uspto-grants-1998_01
Patent number
US05710180

Reaction notes

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