Aniline → HCID 22101180, compound

HRID 1457923Notes

Reaction equation

HRID 1457923 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:15]=1.C(N(C(C)C)CC)(C)C.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1.O>[C:41]1([NH:40][C:5]([NH:13][C:14]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:15]=2)=[O:11])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 15703582HCID 15703582, compound

Product 1

HCID 22101180HCID 22101180, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

To a solution of triphosgene (35.7 mg) in THF (2 ml), was slowly added a solution of 3-amino-1-benzyl-4-ethoxycarbonylpyrazole (30 mg) and diisopropylethylamine (0.0936 ml) in THF (1 ml) over 15 min, and the resulted mixture was stirred at 40° C. for 5 h. To this, was added a solution of aniline (0.0111 ml) and diisopropylethylamine (0.0936 ml) in THF (1 ml), and the resulted mixture was further stirred to react. After completion of the reaction, water was added followed by evaporation under reduced pressure. Ether was added to the residue to crystallize the title compound (32 mg, yield 71%). The product gave the similar 1H-NMR spectrum to an authentic sample prepared by a reported method [Chem. Pharm. Bull., 20, 391-397 (1972)].

Workup

  1. stirringthe resulted mixture was further stirred
  2. customto react
  3. additionwas added
  4. customfollowed by evaporation under reduced pressure
  5. additionEther was added to the residue

Sources & evidence

ORD record
ord-8b2c42070d844b9991ad9f34e9cb0a8f
Source dataset
uspto-grants-1998_12
Patent number
US05849779

Reaction notes

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