Chlorine → HCID 20371654, compound

HRID 616214Notes

Reaction equation

HRID 616214 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:27]=[CH:26][C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([CH:22]=[CH:23][C:24]=2[OH:25])[CH:14]([OH:21])[CH2:15][NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:9])=[CH:6][CH:5]=1.C(O)(=O)C.ClCl.ClCl>C(O)(=O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([CH:22]=[C:23]([Cl:1])[C:24]=2[OH:25])[CH:14]([OH:21])[CH2:15][NH:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:9])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 20371624HCID 20371624, compoundHCID 88629652HCID 88629652, compound

Product 1

HCID 20371654HCID 20371654, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of 3-(4-methoxybenzamido)-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride (0.5 g, 0.0013 mole) in glacial acetic acid (5 ml) a glacial acetic acid/chlorine solution (11.86 ml) containing 0.0898 g (0.0013 mole) of chlorine was added at room temperature with stirring during 10 minutes. The mixture was kept with continued stirring for 24 hours at room temperature, whereafter insoluble substance was filtered off, washed with ether, and air-dried (160 mg) (32%), melting point 196° - 199° C. 80 mg of the crude product was recrystallized from methanol (2 ml) (insoluble substance was filtered off). The yield of the analytically pure 3-(4-methoxybenzamido)-4-hydroxy-5-chloro-α-(tert.butylaminomethyl)benzylalcohol hydrochloride was 50 mg (20%), m.p. 205° - 206° C.

Workup

  1. additionwas added at room temperature
  2. stirringwith continued stirring for 24 hours at room temperature, whereafter insoluble substance
  3. filtrationwas filtered off
  4. washwashed with ether
  5. customair-dried (160 mg) (32%), melting point 196° - 199° C
  6. custom80 mg of the crude product was recrystallized from methanol (2 ml) (insoluble substance was filtered off)

Sources & evidence

ORD record
ord-3e76d0daee87468bbea07a7f6a226f43
Source dataset
uspto-grants-1978_02
Patent number
US04072760

Reaction notes

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