N,N-Diethylaniline → HCID 12054386, compound

HRID 1578957Notes

Reaction equation

HRID 1578957 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178418869HCID 178418869, compound

Product 1

HCID 12054386HCID 12054386, compound

Procedure

A stirred mixture of 32.1 g of (4-hydroxy-2-pyrimidinylthio)acetic acid, ethyl ester and 22.4 g of N,N-diethylaniline in 400 ml. of phosphorus oxychloride were heated under reflux for 5 hr. The phosphorus oxychloride was removed in a rotary evaporator in vacuo. The residue was poured onto ice and the mixture was extracted with 1 liter of ether. The ether solution was dried over MgSO4 and then filtered. The filtrate was taken to dryness in a rotary evaporator yielding 22.9 g of (4-chloro-2-pyrimidinylthio)acetic acid, ethyl ester (an oil). This material was used directly in the next step without purification.

Workup

  1. temperatureunder reflux for 5 hr
  2. customThe phosphorus oxychloride was removed in a rotary evaporator in vacuo
  3. additionThe residue was poured onto ice
  4. extractionthe mixture was extracted with 1 liter of ether
  5. dry with materialThe ether solution was dried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was taken to dryness in a rotary evaporator

Sources & evidence

ORD record
ord-10b9a2c8c97b4919a92a96012e341be3
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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