Water → 11H-imidazo[1,2-c][1,3]benzodiazepin-5(6H)-one

HRID 2164810Notes

Reaction equation

HRID 2164810 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[CH2:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1.C(N(CC)CC)C.O>C(#N)C>[N:19]1[CH:18]=[CH:17][N:16]2[C:15]=1[CH2:14][C:13]1[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=1[NH:11][C:2]2=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 133449032-[(1H-Imidazol-2-yl)methyl]aniline

Product 1

HCID 1334492211H-imidazo[1,2-c][1,3]benzodiazepin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 32.4 g of phenyl chloroformate in 100 ml of acetonitrile is added dropwise under nitrogen while stirring to a mixture of 34.6 g of 2-(2-aminobenzyl)imidazole and 71 g of triethylamine in 600 ml of acetonitrile at room temperature. After addition is complete, the reaction mixture is heated under reflux for 12 hours, and allowed to cool to room temperature. Water (150 ml) is added, the mixture is stirred at room temperature for 0.5 hour and cooled to 5°. The resulting precipitate is filtered off, washed first twice with 50 ml of water, then 3 times with 33 ml of cold acetone and dried to give 11H-imidazo[1,2-c][1,3]benzodiazepin-5-(6H)-one, m.p. 255°-7°.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 12 hours
  4. temperaturecooled to 5°
  5. filtrationThe resulting precipitate is filtered off
  6. washwashed first twice with 50 ml of water
  7. dry with material3 times with 33 ml of cold acetone and dried

Sources & evidence

ORD record
ord-95062da6924f42adbb0312cc18dccb4b
Source dataset
uspto-grants-1985_03
Patent number
US04507311

Reaction notes

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