Potassium cyanate → HCID 67577951, compound

HRID 361710Notes

Reaction equation

HRID 361710 reaction equation
[O-:1][C:2]#[N:3].[K+].[ClH:5].Cl.[CH2:7]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][NH:25][CH:26]([CH3:28])[CH3:27])[NH2:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.Cl>[ClH:5].[CH2:7]([C:14]1[CH:15]=[C:16]([NH:17][C:2]([NH2:3])=[O:1])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][NH:25][CH:26]([CH3:28])[CH3:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 67578945HCID 67578945, compound

Product 1

HCID 67577951HCID 67577951, compoundYield 283.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Potassium cyanate (44 mg) was added to a stirred solution of 3-benzyl-4-(3-[N-isopropylamino]propoxy)aniline dihydrochloride (222 mg) in water (5 mls). The reaction mixture was stirred for 2 hours and the resulting precipitate collected by filtration. The solid collected was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 90:10:1 (v/v/v) mixture of dichloromethane/ethanol/ammonia (density=0.88 g/cm3) as eluent to give a residue which was dissolved in saturated methanolic hydrogen chloride solution. The solution was evaporated to give a solid which was crystallised from ethanol to give 3-benzyl-4-(3-[N-isopropylamino]propoxy)phenylurea hydrochloride as a white solid (582 mg), m.p. 204.7° C., microanalysis, found: C, 63.6; H, 7.6; N, 10.9%; C20H23N3O. HCl requires: C, 63.6; H, 7.47; N, 11.1%; NMR:([CD3 ]2SO): 1.2(6H,d), 2.05(2H,m), 2.9(2H,t), 3.25(1H,m), 3.85(2H,s), 4.0(2H,t), 5.7(2H,s), 6.82(1H,d), 7.05-7.3(7H,m), 8.4(1H,s), 7.5(2H,s); m/z 342(M+H).

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. customThe solid collected
  3. customwas purified by flash column chromatography on silica gel (Merck Art No 9385)
  4. additiona 90:10:1 (v/v/v) mixture of dichloromethane/ethanol/ammonia (density=0.88 g/cm3) as eluent
  5. customto give a residue which
  6. customThe solution was evaporated
  7. customto give a solid which
  8. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-be0b653d168e43ea9b064af3edfb602a
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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