Chloroacetyl chloride → HCID 20213180, compound

HRID 1388997Notes

Reaction equation

HRID 1388997 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]([S:16][CH3:17])=[N:12][N:11]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:18][CH2:19][C:20]([N:9]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:8])[C:10]1[N:14]([CH3:15])[C:13]([S:16][CH3:17])=[N:12][N:11]=1)=[O:21]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 20213179HCID 20213179, compound

Product 1

HCID 20213180HCID 20213180, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 6.1 g (0.0232 mol) 3-(2,6-dimethylphenylamino)-4-methyl-5-methylthio-1,2,4-triazole in 150 ml toluene was added quickly 2.7 g (0.024 mol) chloroacetyl chloride. An exotherm ensued and the temperature rose to 100° C., followed by separation of an oil which solidified. The reaction mixture was stirred at 100°-105° C. for 1 hour, cooled and diluted with 50 ml saturated sodium bicarbonate and 20 ml dichloromethane. The clear organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give a clear oil. The oil was crystallized from ethyl ether to give 7.4 g of product, as a pale yellow solid, m.p. 145°-147° C. The product is tabulated in Table I as Compound No. 14-B.

Workup

  1. customrose to 100° C.
  2. customfollowed by separation of an oil which
  3. temperaturecooled
  4. additiondiluted with 50 ml saturated sodium bicarbonate and 20 ml dichloromethane
  5. customThe clear organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto give a clear oil
  9. customThe oil was crystallized from ethyl ether

Sources & evidence

ORD record
ord-e5497dffc1aa439fa6229978dbce9c63
Source dataset
uspto-grants-1981_01
Patent number
US04243408

Reaction notes

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