Tyrosol → HCID 14328859, compound

HRID 867860Notes

Reaction equation

HRID 867860 reaction equation
C([O:4][CH:5]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:8]=2[NH:7][C:6]1=[O:23])(=O)C.[OH:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]O)=[CH:27][CH:26]=1>CN(C)C=O>[Cl:22][C:19]1[CH:20]=[CH:21][C:8]2[NH:7][C:6](=[O:23])[CH:5]([O:4][CH2:30][CH2:29][C:28]3[CH:32]=[CH:33][C:25]([OH:24])=[CH:26][CH:27]=3)[N:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:9]=2[CH:18]=1

Participants

4

Reactant 2

HCID 10393TyrosolHCID 1026977-chloro-1,3-dihydro-5-phenyl-2-oxo-2H-1,4-benzodiazepin-3-yl acetate

Product 1

HCID 14328859HCID 14328859, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10.0 grams (0.0309 mol) of 3-acetoxy-7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-one and 11.0 grams (0.080 mol) of 4-hydroxyphenethylalcohol (Aldrich) in 50 ml. dry N,N-dimethylformamide was stirred in an ice bath and hydrogen chloride gas was bubbled into the solution for 5-10 minutes. After standing at room temperature for 18 hours, the reaction mixture was poured onto ice and the pH adjusted to 7.5 with ammonium hydroxide. The mixture was filtered and the gummy precipitate was stirred with 50 ml. dichloromethane and 50 ml. water for 5 minutes and filtered. The solid was crystallized from a mixture of dichloromethane and methanol to give 9.6 grams (77%) of the compound of Formula I (a) as white rods, m.p. 222°-230° C.; 1R (KBr) 3310, 3215, 3140, (OH,NH), 1685 cm-1 (C=O); NMR (DMSO-d6) 2.86 (t, 2H, CH2Ar), 3.77, 3.95 (2q, 2H, CH2O), 4.78 (s, 1H, CH), 6.68, 7.09 (2d, 4H, aromatics), 9.18 (s, 1H, OH), 10.81 (s, 1H, NH); mass spectrum m/e 406 (M+ ) Anal. Calcd for C23H19ClN2O3 : C, 67.90; H, 4.71; N, 6.89. Found: C, 67.91; H, 4.83; N, 6.80.

Workup

  1. customhydrogen chloride gas was bubbled into the solution for 5-10 minutes
  2. additionthe reaction mixture was poured onto ice
  3. filtrationThe mixture was filtered
  4. waitwater for 5 minutes
  5. filtrationfiltered
  6. customThe solid was crystallized from a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-92fcf4104a88454a944cfa6daf396e25
Source dataset
uspto-grants-1988_10
Patent number
US04777169

Reaction notes

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