Ammonia → HCID 22125505, compound

HRID 1858021Notes

Reaction equation

HRID 1858021 reaction equation
[ClH:1].C([C:4]1[C:12]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:11]([NH2:22])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[NH:7])C.N>C(O)C>[ClH:1].[NH2:22][C:11]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][C:12]=1[NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22125600HCID 22125600, compound

Product 1

HCID 22125505HCID 22125505, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising ethyl 4-amino-3-phenethylaminobenzamidine hydrochloride (0.68, 2.1 mmol) and 2M ammonia in ethanol (20 mL) was heated at 90° C. in a sealed reaction container for 2.5 hours. The container was vented and the mixture was concentrated under reduced pressure to provide 4-amino-3-phenethylaminobenzamidine hydrochloride (0.4 g, 1.2 mmol) as a brown foam. 1H-NMR (300 Mhz, DMSO-d6): 2.9 (t, 2H), 3.4 (m, 2H), 5.1 (m, 1H), 5.8 (s, 2H), 6.6 (d, 1H), 6.8 (s, 1H), 7.1 (d, 1H), 7.3 (m, 5H), 8.6 (s, 2H), 8.7 (s, 2H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4be5431b17544149bd296e1ffae36b29
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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