Toluene → HCID 178509087, compound

HRID 57761Notes

Reaction equation

HRID 57761 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].O=[C:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40](=O)[CH2:41][NH:42]/[C:43](/[NH:52]C(OC(C)(C)C)=O)=[N:44]\C(OC(C)(C)C)=O)[CH2:17][NH:18]/[C:19](/[NH:28]C(OC(C)(C)C)=O)=[N:20]\C(OC(C)(C)C)=O>O>[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[CH2:39]([C:40]1[NH+:44]=[C:43]([NH2:52])[NH:42][CH:41]=1)[CH2:38][CH2:37][CH2:36][C:16]1[NH+:20]=[C:19]([NH2:28])[NH:18][CH:17]=1.[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acid2×HCID 178454273(E,E)-1,1'-(2,7-Dioxooctane-1,8-diyl)bis(2',3-dibocguanidine)

Product 1

HCID 178509087HCID 178509087, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Toluene (40 mL) and trifluoroacetic acid (650 μL, 8.36 mmol, 10.0 equiv) were added via syringe to a flask charged with ketoguanidine 75 (549 mg, 0.836 mmol, 1 equiv) and the resulting mixture was heated to 75° C. After 16 h, the reaction mixture was allowed to cool to 23° C. and was concentrated under reduced pressure. Water (20 mL) and trifluoroacetic acid (650 μL, 8.36 mmol, 10.0 equiv) were added via syringe to the residue and the resulting mixture was heated to 100° C. After 45 h, the reaction mixture was allowed to cool to 23° C. and was concentrated under reduced pressure to give 2-aminoimidazole 76 (375 mg, 100%) as a brown solid. 1H NMR (500 MHz, CD3OD, 21° C.): δ 6.49 (s, 2H), 2.53 (app-t, J=6.5 Hz, 4H), 1.65 (app-t, J=7.1 Hz, 4H). 13C NMR (125.8 MHz, CD3OD, 21° C.): δ 162.6, 148.8, 128.8, 109.8, 101.4, 28.7, 25.2. FTIR (neat) cm−1: 3179 (br-s), 2361 (w), 1702 (s), 1442 (m), 1205 (s), 1134 (s), 845 (m), 723 (m). HRMS (ESI) (m/z): calc'd for C10H17N6, [M+H]+: 221.1509, found: 221.1512.

Workup

  1. temperatureto cool to 23° C.
  2. concentrationwas concentrated under reduced pressure
  3. temperaturethe resulting mixture was heated to 100° C
  4. waitAfter 45 h
  5. temperatureto cool to 23° C.
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c0f602285974419b8294d5dc12bc57d
Source dataset
uspto-grants-2016_09
Patent number
US09434736B2

Reaction notes

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