Ammonia → HCID 178447932, compound

HRID 1463011Notes

Reaction equation

HRID 1463011 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[N:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][N:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(Cl)(Cl)Cl.ClC(OCC)=O.[NH3:29]>C(N(CC)CC)C>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[N:15]=[CH:14][C:13]([C:16]([NH2:29])=[O:18])=[CH:12][N:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 178447936HCID 178447936, compound

Product 1

HCID 178447932HCID 178447932, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
2 °C

Procedure

A solution of 13.85 g of trans-2-(4-propylcyclohexyl)-5-pyrimidinecarboxylic acid, 260 ml of chloroform and 7.8 ml of triethylamine is cooled to 2° C. and treated with 5.32 ml of ethyl chloroformate. The mixture is stirred at 2° C. for 15 minutes and then a strong stream of ammonia gas is conducted in for 10 minutes (while cooling with an ice-bath). The resulting suspension is stirred at 20° C. for a further 1 hour and then evaporated in vacuo. The solid residue is stirred up with 210 ml of water for 45 minutes and then filtered off under suction and dried. There are obtained 9.6 g of crude trans-2-(4-propylcyclohexyl)-5-pyrimidinecarboxamide (m.p. 234°-235° C.) which can be purified by sublimation at 175° C./0.05 mmHg; m.p. 249.3°-250.5° C.

Workup

  1. stirringThe resulting suspension is stirred at 20° C. for a further 1 hour
  2. customevaporated in vacuo
  3. stirringThe solid residue is stirred up with 210 ml of water for 45 minutes
  4. filtrationfiltered off under suction
  5. customdried

Sources & evidence

ORD record
ord-723c250cc99c4f46ac912282ebaa62f6
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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