Trifluoroacetic anhydride → 2-Phenylcarbonylaminoimidazole

HRID 1576098Notes

Reaction equation

HRID 1576098 reaction equation
O1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.F[C:10](F)(F)[C:11](OC(=O)C(F)(F)F)=O.Cl.[NH2:23][C:24]1[NH:25][CH:26]=[CH:27][N:28]=1>O1CCCC1.C(N(CC)CC)C>[C:3]1([C:6]([NH:23][C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)=[O:8])[CH:4]=[CH:5][CH:11]=[CH:10][CH:2]=1

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 102683-Furoic acidHCID 122112381H-Imidazol-2-amine hydrochloride

Product 1

HCID 128479352-Phenylcarbonylaminoimidazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 3-furoic acid in 50 ml. of tetrahydrofuran, there is added 10.5 g. of trifluoroacetic anhydride. To the resulting solution, after 30 minutes and at 20°-25°C., there is added 15 ml. of triethylamine and 4.1 g. of 2-aminoimidazole hydrochloride and 20 ml. of tetrahydrofuran. The thus-obtained reaction mixture is allowed to stand overnight at 20° -25°C., followed by concentration, dilution with water, filtration and recrystallization from methanol to yield 2-(3-furylcarbonylamino)-imidazole [(III), R = 3-furyl], identical to that obtained in Example 1A.

Workup

  1. additionat 20°-25°C., there is added 15 ml
  2. customThe thus-obtained reaction mixture
  3. waitto stand overnight at 20° -25°C.
  4. concentrationfollowed by concentration, dilution with water, filtration and recrystallization from methanol

Sources & evidence

ORD record
ord-bec33d4d575144318f08ca844b669bac
Source dataset
uspto-grants-1976_09
Patent number
US03979404

Reaction notes

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