Dichloromethane → HCID 178448009, compound

HRID 1731280Notes

Reaction equation

HRID 1731280 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=O)=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].C(Cl)Cl>CN(C=O)C>[C:25]([C:24]1[CH:28]=[CH:29][C:21]([C@H:18]2[CH2:17][CH2:16][C@H:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11]3)[CH2:20][CH2:19]2)=[CH:22][CH:23]=1)#[N:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178448010HCID 178448010, compound

Product 1

HCID 178448009HCID 178448009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 32.6 g of p-(trans-4-(trans-4-propyl-cyclohexyl)-cyclohexyl)-acetophenone in 100 ml of dioxane is added dropwise to a solution of 40 g of NaOH and 48 g of bromine in 230 ml of water at 20°, while stirring. Stirring is continued for 1 hour. A solution of 14 g of NaHSO3 in 140 ml of water is added and hydrochloric acid is added until the pH is 5. Customary working up (CH2Cl2) gives p-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-benzoic acid. The crude product is boiled with 60 ml of SOCl2 for 2.5 hours. After evaporation, the resulting crude acid chloride is dissolved in 430 ml of dioxane, 200 ml of 25% aqueous ammonia is added and the mixture is poured onto ice and filtered to give p-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-benzamide. 65 g of POCl3 is added dropwise to a solution of 32.7 g of this amide in 500 ml of DMF at 50°, while stirring. After the mixture has been further stirred for 1 hour, it is poured onto ice and worked up in the customary manner (CH2Cl2) to give trans-1-p-cyanophenyl-4-(trans-4-propyl-cyclohexyl)-cyclohexane, m.p. 55°, c.p. 184°.

Workup

  1. stirringAfter the mixture has been further stirred for 1 hour
  2. additionit is poured onto ice

Sources & evidence

ORD record
ord-561eac727106401d9929a55a3bbaf56f
Source dataset
uspto-grants-1986_11
Patent number
US04620938

Reaction notes

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