Isopropylamine → HCID 178457549, compound

HRID 1788631Notes

Reaction equation

HRID 1788631 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)#[N:2].[CH:18]([NH2:21])([CH3:20])[CH3:19]>C(#N)C>[C:1]([N:3]=[C:4]([NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)[NH:21][CH:18]([CH3:20])[CH3:19])#[N:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 178503884HCID 178503884, compound

Product 1

HCID 178457549HCID 178457549, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 30.0 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)-S-methylisothiourea and 40 ml of isopropylamine in 300 ml of acetonitrile was heated at reflux with stirring for 154 hours. The solvent and excess isopropylamine were removed by evaporation in vacuo, leaving the crude product as a tacky, white solid. Crystallization from isopropyl acetate followed by a recrystallization from a mixture of isopropyl acetate and 2-propanol gave 5.13 g of N"-cyano-N-isopropyl-N'-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as a white, crystalline solid, mp 170.5°-172.5° C.

Workup

  1. temperatureat reflux
  2. customThe solvent and excess isopropylamine were removed by evaporation in vacuo
  3. customleaving the crude product as a tacky, white solid
  4. customCrystallization from isopropyl acetate
  5. customfollowed by a recrystallization from a mixture of isopropyl acetate and 2-propanol

Sources & evidence

ORD record
ord-db048911c46a4e7fbece0f2029e0bf2d
Source dataset
uspto-grants-1987_08
Patent number
US04684398

Reaction notes

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