Hydrochloric Acid → HCID 178447931, compound

HRID 1463006Notes

Reaction equation

HRID 1463006 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[N:25]=[CH:24][C:23]([C:26]([NH2:28])=O)=[CH:22][N:21]=2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].N1C=CC=CC=1.Cl>CCOCC>[CH2:11]([C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]2[N:25]=[CH:24][C:23]([C:26]#[N:28])=[CH:22][N:21]=2)[CH2:18][CH2:19]1)[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178447932HCID 178447932, compound

Product 1

HCID 178447931HCID 178447931, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

20.3 g of benzenesulphonyl chloride are added while stirring to a mixture of 9.45 g of trans-2-(4-propylcyclohexyl)-5-pyrimidinecarboxamide and 55 ml of pyridine. After 2 hours, the solution is poured into a mixture of 100 g of ice and 0.9 ml of half-concentrated hydrochloric acid. The precipitated product is taken up in ether and the ether extract is washed neutral with water, dried and evaporated. The crude product is purified by chromatography on 200 g of silica gel with hexane/benzene (1:1) and subsequent bulb-tube distillation at 135° C./0.05 mmHg. There is obtained trans-2-(4-propylcyclohexyl)-5-pyrimidinecarbonitrile; m.p. 74° C., cl.p 89.5° C., smectic-nematic phase transition 71.5° C. (monotropic).

Workup

  1. extractionthe ether extract
  2. washis washed neutral with water
  3. customdried
  4. customevaporated
  5. distillationThe crude product is purified by chromatography on 200 g of silica gel with hexane/benzene (1:1) and subsequent bulb-tube distillation at 135° C./0.05 mmHg

Sources & evidence

ORD record
ord-69826bfd94bf4826b63bc3ae5b1f7dd4
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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