Hydrochloric Acid → HCID 23468278, compound

HRID 443649Notes

Reaction equation

HRID 443649 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([N:5]([CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:36](Cl)(=[O:38])[CH3:37].Cl>>[F:1][C:2]([F:30])([F:31])[C:3]([N:5]([CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:36](=[O:38])[CH3:37])=[CH:22][CH:21]=1)[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 23468288HCID 23468288, compound

Product 1

HCID 23468278HCID 23468278, compound

Procedure

To a solution of 5.4 g. of ethyl 4-[N-trifluoroacetyl-2-(1-naphthyloxy)ethylamino]benzoate and 5.7 g. of anhydrous aluminum chloride at 0° C. is added 1.1 g. of acetyl chloride with stirring. After 1 hour at 0° C., the solution is poured over 200 g. of ice plus 20 ml. concentrated hydrochloric acid. The organic phase is separated and the aqueous phase re-extracted. After washing with dilute acid, the methylene chloride extract is evaporated to dryness. The residue is crystallized from acetonitrile, m.p. 160°-161° C.

Workup

  1. additionthe solution is poured over 200 g
  2. customThe organic phase is separated
  3. extractionthe aqueous phase re-extracted
  4. washAfter washing
  5. additionwith dilute acid
  6. extractionthe methylene chloride extract
  7. customis evaporated to dryness
  8. customThe residue is crystallized from acetonitrile, m.p. 160°-161° C.

Sources & evidence

ORD record
ord-6b1b83ca46b44873a84f4134def3b41c
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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