2-Tolyl isocyanate → HCID 21837096, compound

HRID 1419987Notes

Reaction equation

HRID 1419987 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][C:3]=1C.[C:25]1([CH3:34])[C:26]([N:31]=[C:32]=[O:33])=[CH:27][CH:28]=[CH:29][CH:30]=1>O1CCCC1>[CH3:34][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:22][CH:23]=1)=[O:33]

Participants

4

Reactant 2

HCID 691942-Tolyl isocyanateHCID 1068697510,11-Dihydro-10-(4-amino-3-methylbenzoyl)-5H-Pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 21837096HCID 21837096, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.93 g 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.37 g of o-tolyl isocyanate in 50 ml of tetrahydrofuran is heated at reflux under argon for 24 hours. The volatiles are evaporated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 0.68 g of the desired product as crystals, m.p. 155°-158° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under argon for 24 hours
  3. customThe volatiles are evaporated in vacuo to a residue which
  4. dissolutionis dissolved in methylene chloride
  5. additionHexane is added to the filtrate at the boil

Sources & evidence

ORD record
ord-9254b659056f4692958168b696be9e5f
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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