Toluene → HCID 178512346, compound

HRID 543245Notes

Reaction equation

HRID 543245 reaction equation
[C:1]([NH:3][C:4](=[NH:12])OC1C=CC=CC=1)#[N:2].[CH:13]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.NC(=N)O.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([NH:3][C:4](=[NH:12])[NH:23][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)#[N:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 178512385HCID 178512385, compoundHCID 178513210HCID 178513210, compound

Product 1

HCID 178512346HCID 178512346, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.3 g of N-cyano-O-phenylisourea and 1.2 g of 1,2,3,4-tetrahydro-1-naphthylamine in 5 ml of chloroform was heated at reflux in an oil bath. Disappearance of the isourea was monitored by thin layer chromatography analysis. After 30 hours, the resulting thick solution was treated with 5 ml of toluene and allowed to stand at room temperature which resulted in the crystallization of the desired product. The supernatant solution was withdrawn and the product washed with toluene (10 ml). Upon drying under vacuum, 0.91 g of the desired compound was obtained. A second crop of crystals was collected after concentrating the mother liquor slightly. Total yield of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)guanidine was 1.29 g, mp 153°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in an oil bath
  3. customto stand at room temperature

Sources & evidence

ORD record
ord-d3b31eb3f94742aaa49a71b870f28551
Source dataset
uspto-grants-1987_04
Patent number
US04661520

Reaction notes

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