Triethylamine → HCID 18801449, compound

HRID 597465Notes

Reaction equation

HRID 597465 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([N+:16]([O-:18])=[O:17])=[C:11]([CH3:19])[N:10]=1.[CH:20]([NH2:24])([CH2:22][CH3:23])[CH3:21]>C(O)C>[Cl:8][C:9]1[N:14]=[C:13]([NH:24][CH:20]([CH2:22][CH3:23])[CH3:21])[C:12]([N+:16]([O-:18])=[O:17])=[C:11]([CH3:19])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24874Sec-ButylamineHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidine

Product 1

HCID 18801449HCID 18801449, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 ml of triethylamine are added to a solution of 15.6 g of 2,4-dichloro-5-nitro-6-methylpyrimidine (0.075 mole) in 300 ml of absolute ethanol. With ice cooling, 6.6 g of sec. butylamine (0.09 mole) are added dropwise at 0°-5° C over the course of c. 40 minutes to the dark red solution. After the mixture has been stirred for c. 3/4 hour at this temperature, it is poured into c. 700 ml of ice water and the water is extracted 3 times with ether. The ethereal extracts are dried over magnesium sulphate and evaporated. The resultant red oily substance is crystallised from petroleum ether to yield 10.5 g of 2-chloro-4-sec. butylamino-5-nitro-6-methyl-pyrimidine of m.p. 40°-43° C.

Workup

  1. custom40 minutes
  2. addition3/4 hour at this temperature, it is poured into c
  3. extraction700 ml of ice water and the water is extracted 3 times with ether
  4. dry with materialThe ethereal extracts are dried over magnesium sulphate
  5. customevaporated
  6. customThe resultant red oily substance is crystallised from petroleum ether

Sources & evidence

ORD record
ord-0a1bf8bb37514a25a31e722ca7ff5bd9
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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