Hydrochloric Acid → HCID 178459233, compound

HRID 1680561Notes

Reaction equation

HRID 1680561 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[CH2:11]([O:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH:22]=[N:23][C:24]([C:27]3[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=O)=[CH:29][CH:28]=3)=[N:25][CH:26]=2)[CH2:17][CH2:16]1)[CH2:12][CH3:13].N1C=CC=CC=1.Cl>C(Cl)Cl>[CH2:11]([O:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH:22]=[N:23][C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:31]#[N:33])=[CH:34][CH:35]=3)=[N:25][CH:26]=2)[CH2:17][CH2:16]1)[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178459234HCID 178459234, compound

Product 1

HCID 178459233HCID 178459233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

9.2 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 16.0 g. of trans-p-[5-(4-n-propyloxycyclohexyl)-2-pyrimidinyl]benzamide in 170 ml. of pyridine. The mixture is then warmed to 40° C. for 15 hours in an oil-bath. The clear mixture is poured into a mixture of 200 g. of ice and 24.1 ml. of concentrated hydrochloric acid and the product is taken up in methylene chloride. The extract is washed three times with 195 ml. of 3-N hydrochloric acid each time, then with 100 ml. of saturated sodium bicarbonate solution and with water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 200 g. of silica gel with benzene and with benzene containing 1% and 2% acetone (v/v). The fractions which are pure according to thin-layer chromatography are recrystallized from acetone/hexane. There is obtained trans-p-[5-(4-n-propyloxycyclohexyl)-2-pyrimidinyl]benzonitrile; melting point 114.5° C., clearing point 223.5° C.

Workup

  1. additionThe clear mixture is poured into a mixture of 200 g
  2. washThe extract is washed three times with 195 ml
  3. dry with materialof saturated sodium bicarbonate solution and with water, dried over sodium sulfate
  4. customevaporated
  5. customThe crude product is chromatographed on a column of 200 g
  6. customare recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-d8760a32716342a58ed27caf7ee514db
Source dataset
uspto-grants-1981_06
Patent number
US04273929

Reaction notes

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