Isopropylamine → HCID 178457549, compound

HRID 2309001Notes

Reaction equation

HRID 2309001 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-9c8d5ab657c24055bd20e5695afe0cdd
Source dataset
uspto-grants-1987_09
Patent number
US04692467

Reaction notes

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