Ammonia → Ethyl 2-[(4-amino-6-chloro-2-pyrimidinyl)thio]acetate

HRID 1578934Notes

Reaction equation

HRID 1578934 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH3:22]>>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][S:9][C:4]1[N:5]=[C:6]([NH2:22])[CH:7]=[C:2]([Cl:1])[N:3]=1)[CH3:15]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 54015358Ethyl 2-[(4-amino-6-chloro-2-pyrimidinyl)thio]acetate

Procedure

A mixture of 10.7 g of (4,6-dichloro-2-pyrimidinylthio) acetic acid, ethyl ester and 4.2 g of sodium carbonate in 150 ml. of saturated ethanolic ammonia solution was stirred at room temperature for 1 week. The reaction mixture was filtered and petroleum ether was added to the filtrate until a precipitate was formed. The precipitate was recrystallized from petroleum ether-ethanol to give 1.2 g of product, mp. 113°-116°C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionpetroleum ether was added to the filtrate until a precipitate
  3. customwas formed
  4. customThe precipitate was recrystallized from petroleum ether-ethanol

Sources & evidence

ORD record
ord-5a1e35460015479ea59300d97545c25b
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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