Dimethylamine → HCID 13882888, compound

HRID 542124Notes

Reaction equation

HRID 542124 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[CH3:21][NH:22][CH3:23]>O.CN(C=O)C>[CH3:21][N:22]([CH3:23])[C:7]1[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=[C:3]([C:2]([F:20])([F:19])[F:1])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882888HCID 13882888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.67 g (0.024 mol) of product of Example 19 and 5.4 g (0.048 mol) of 40% solution of dimethylamine in H2O and 50 ml of DMF was stirred for three hours. The temperature rose to 48° C. and dropped back down to room temperature. The reaction mixture was poured into H2O, extracted with ether, washed with diluted HCl, dried (MgSO4) and concentrated in vacuo to 6.63 g of solid which was recrystallized in hot hexane affording 6.01 g (75.8%) of product as a white solid; mp 63.5°-65° C.

Workup

  1. customrose to 48° C.
  2. additiondropped back down to room temperature
  3. extractionextracted with ether
  4. washwashed with diluted HCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to 6.63 g of solid which
  7. customwas recrystallized in hot hexane affording 6.01 g (75.8%) of product as a white solid

Sources & evidence

ORD record
ord-f748ac5ffed849f88573ebdffcee5852
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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