Ammonia → HCID 178444457, compound

HRID 1249312Notes

Reaction equation

HRID 1249312 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1C=CC=CC=1.S(Cl)(Cl)=O.[NH3:39]>O1CCOCC1.O>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:39])=[O:25])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 241BenzeneHCID 24386Thionyl ChlorideHCID 178444458HCID 178444458, compound

Product 1

HCID 178444457HCID 178444457, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3.1 g of crude p-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]benzoic acid, 50 ml of benzene and 0.9 ml of thionyl chloride was heated to boiling for 2 hours. Benzene and excess thionyl chloride were distilled off in vacuo. The residue was taken up twice in 50 ml of toluene and concentrated each time. The crude acid chloride obtained (3.5 g) was dissolved in 50 ml of dioxan and the solution was allowed to flow into a mixture of 18 ml of concentrated ammonia and 75 ml of dioxan. The resulting suspension was stirred at room temperature for 1 hour, then diluted with water and suction filtered. The material on the suction filter was washed neutral with water and then dried by concentration with toluene. 2.6 g of crude p-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]benzamide were obtained.

Workup

  1. temperaturewas heated
  2. distillationBenzene and excess thionyl chloride were distilled off in vacuo
  3. concentrationconcentrated each time
  4. customThe crude acid chloride obtained (3.5 g)
  5. filtrationfiltered
  6. filtrationThe material on the suction filter
  7. washwas washed neutral with water
  8. dry with materialdried by concentration with toluene

Sources & evidence

ORD record
ord-74ffb6b368b9455b88cb9e5c7882c9bd
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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