Dichloromethane → 11H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione

HRID 1462171Notes

Reaction equation

HRID 1462171 reaction equation
ClCCl.C(N(CC)CC)C.[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:24](Cl)(Cl)=[S:25]>C(Cl)(Cl)(Cl)Cl>[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:24]2=[S:25]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 133449032-[(1H-Imidazol-2-yl)methyl]aniline

Product 1

HCID 1334490411H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Dichloromethane (42,000 ml) and 5,120 g (50.65 moles) of triethylamine were charged into a 20 gallon flask. The solution was stirred under nitrogen atmosphere and 4,370 g (25.23 moles) of 2-(2-aminobenzyl)imidazole were added. The suspension was cooled to 0°-5° and 3,421 g (29.75 moles) of 85% thiophosgene in carbon tetrachloride were added over 3 hours, during which time the reaction temperature rose slowly to 15°. The suspension was then stirred at 10° for 4 hours and at ambient temperature overnight. The precipitated product was collected, washed with 2×3000 ml of dichloromethane and 5×4000 ml of water, and dried (5 mm Hg/60°) to give 11H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione, m.p. 182°-183°.

Workup

  1. temperatureThe suspension was cooled to 0°-5°
  2. customrose slowly to 15°
  3. stirringThe suspension was then stirred at 10° for 4 hours and at ambient temperature overnight
  4. customThe precipitated product was collected
  5. washwashed with 2×3000 ml of dichloromethane and 5×4000 ml of water
  6. customdried (5 mm Hg/60°)

Sources & evidence

ORD record
ord-b52160a548d34f7c8cf32908e8d8ee52
Source dataset
uspto-grants-1984_07
Patent number
US04459232

Reaction notes

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