2-Toluidine hydrochloride → N-(Adamantan-1-yl)-N'-(2-methylphenyl)guanidine

HRID 1451279

Reaction equation

HRID 1451279 reaction equation
[C:1]12([NH:11][C:12]#[N:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[NH2:15][C:16]1[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1>ClC1C=CC=CC=1>[C:1]12([NH:11][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])=[NH:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 124842-Toluidine hydrochlorideHCID 124358461-Adamantylcyanamide

Product 1

HCID 178424367N-(Adamantan-1-yl)-N'-(2-methylphenyl)guanidine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A suspension of adamantan-1-ylcyanamide (151 mg, 0.857 mmol) and o-toluidine hydrochloride (186 mg, 0.857 mmol) in dry chlorobenzene was heated between 100°-130° C. for 4.5 hrs. The chlorobenzene was evaporated in vacuo with heating and the residue (285 mg) taken up in 18 ml of water. A gummy, insoluble material was discarded. On adjusting the aqueous extract to pH 9-9.5, a precipitate formed (194 mg, 71%). Two recrystallizations from EtOH/H2O gave the analytical sample; mp 160°-161°, 1H (CD3OD) 1.742 (s, 6 H), 2.050 (d, 6H, J=2.4 Hz), 2.029 (s, 3 H), 6.956 (1 H, J=8.1 Hz), 7.056 (t, 1H, J=8.1 Hz), 7.168 (t, 1H, J=7.5 Hz), 7.213 (d, 1H, J=7.5 Hz). Anal. Calcd for C18H25N3 : C, 76.28; H, 8.89; N, 14.83. Found: C, 76.25; H, 8.86; N, 14.60.

Workup

  1. temperaturewas heated between 100°-130° C. for 4.5 hrs
  2. customThe chlorobenzene was evaporated in vacuo
  3. temperaturewith heating
  4. extractionaqueous extract to pH 9-9.5
  5. customa precipitate formed (194 mg, 71%)
  6. customTwo recrystallizations from EtOH/H2O
  7. customgave the analytical sample

Sources & evidence

ORD record
ord-6175103c8988453a8ed48b1ea7827545
Source dataset
uspto-grants-1997_02
Patent number
US05604228

Linked notes

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