Hydrochloric Acid → HCID 13036997, compound

HRID 2059205Notes

Reaction equation

HRID 2059205 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:21](Cl)[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)=[CH:15][CH:14]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[C:19]([C:16]3[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15492894-BromothiobenzamideHCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-one

Product 1

HCID 13036997HCID 13036997, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Fifty ml. of dioxane was used to dissolve 7.43 g. (0.034 mole) of 4-bromothiobenzamide with heating to about 60° C. Then 10.0 g. (0.034 mole) of 4,4'-dimethoxydesyl chloride in 50 ml. of dioxane was added and the mixture was heated to 100° C. for two hours. The mixture was cooled and acidified with 1 N hydrochloric acid. Most of the dioxane was removed in vacuo and the solid formed was filtered. The solid was purified by silica gel chromatography (400 g.), using benzene as the eluting agent. The product had a melting point of about 155°-157° C. and weighed 8.83 g. (57% yield). The mass spectrum showed the expected molecular ions at m/e=451 and 453.

Workup

  1. dissolutionto dissolve 7.43 g
  2. temperatureThe mixture was cooled
  3. customMost of the dioxane was removed in vacuo
  4. customthe solid formed
  5. filtrationwas filtered
  6. customThe solid was purified by silica gel chromatography (400 g.)

Sources & evidence

ORD record
ord-1550e0ee91894de29c3cbd367a88a592
Source dataset
uspto-grants-1982_03
Patent number
US04322428

Reaction notes

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