Isopropyl isocyanate → HCID 20562362, compound

HRID 848139Notes

Reaction equation

HRID 848139 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23]>C(N(CC)CC)C>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:7]1[C:6]2[CH:21]=[C:2]([NH:1][C:26]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:27])[CH:3]=[CH:4][C:5]=2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 922947-Aminoflunitrazepam

Product 1

HCID 20562362HCID 20562362, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5 g (0.018 M) of 7-amino-1,3-dihydro-1-methyl-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one are heated at reflux for 5 hours with 15 ml of isopropylisocyanate and a catalytic amount of triethylamine. The mixture is left to stand at room temperature for 2.5 days, the product crystallising out partially. The solvent is concentrated partially, cooled with ice and the crystallised product is filtered off. After recrystallisation from methylene chloride/ethyl acetate, there is obtained 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-isopropylurea which melts at 185°-188° C. with decomposition.

Workup

  1. waitThe mixture is left
  2. customthe product crystallising out partially
  3. concentrationThe solvent is concentrated partially
  4. temperaturecooled with ice
  5. filtrationthe crystallised product is filtered off
  6. customAfter recrystallisation from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-543560a233ef416cb71b0ff13666caea
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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