N,N-Dimethylcyclohexylamine → HCID 12837109, compound

HRID 1902390Notes

Reaction equation

HRID 1902390 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.CN(C1CCCCC1)C.[Cl:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([NH2:30])[C:26]=1[C:27]([OH:29])=[O:28]>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C:25]2[C:26](=[C:21]([Cl:20])[CH:22]=[CH:23][CH:24]=2)[C:27]([OH:29])=[O:28])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7415N,N-DimethylcyclohexylamineHCID 678794-Fluorobenzoyl chlorideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 12837109HCID 12837109, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
30 °C

Procedure

17.5 parts of 4-fluorobenzoyl chloride and 14 parts of N,N-dimethylcyclohexylamine are introduced simultaneously, from 2 feeds, into a solution of 17.1 parts of 6-chloroanthranilic acid in 230 parts of ethyl acetate at from 10° to 20° C., and the mixture is then stirred for 20 minutes at 30° C. Thereafter, the reaction mixture is washed once with 1 N hydrochloric acid and then with water, a colorless precipitate being formed. The latter is dissolved in ethyl acetate, and the organic phase is again washed with 1 N hydrochloric acid and then with water, dried over magnesium sulfate and evaporated down; 29 parts of N-(4'-fluorobenzoyl)-6-chloroanthranilic acid, of melting point 228°-233° C., are obtained.

Workup

  1. washThereafter, the reaction mixture is washed once with 1 N hydrochloric acid
  2. customwith water, a colorless precipitate being formed
  3. washthe organic phase is again washed with 1 N hydrochloric acid
  4. dry with materialwith water, dried over magnesium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-41a3327660004216863bfcf149f41985
Source dataset
uspto-grants-1982_12
Patent number
US04363651

Reaction notes

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