Water → HCID 14555673, compound

HRID 1723409Notes

Reaction equation

HRID 1723409 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27])=[CH:14][CH:13]=1.O>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:2][OH:3])=[O:27])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20025664HCID 20025664, compound

Product 1

HCID 14555673HCID 14555673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold stirring suspension of 1 gm hydroxylamine hydrochloride and 1.3 gm sodium carbonate in 25 ml CH2Cl2 was added dropwise 1.58 gms 9(4-methoxyphenyl)nonanoyl chloride over a period of 15 min. The mixture was then stirred in the cold for a further 45 min, then 1.5 ml H2O was added, the mixture was allowed to warm up to room temperature, and stirring was continued for 72 hrs. The precipitated solid was filtered, washed with water, and crystallized twice from CH2Cl2 to give A. The filtrate from the reaction mixture was evaporated in vacuo to give a granular solid which was also crystallized twice from CH2Cl2 to give B. A and B were shown to be the same by spectral comparison. Total yield (A+B)=1.58 gm (51%) m.p. 96°-98° C. Elemental analysis: calculated C 67.90, H 8.90, N 4.95. Found C 67.96, H 9.08, N 4.95 (calculated for 0.2 moles H2O).

Workup

  1. stirringThe mixture was then stirred in the cold for a further 45 min
  2. stirringstirring
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customcrystallized twice from CH2Cl2
  6. customto give A
  7. customThe filtrate from the reaction mixture was evaporated in vacuo
  8. customto give a granular solid which
  9. customwas also crystallized twice from CH2Cl2
  10. customto give B
  11. customTotal yield (A+B)=1.58 gm (51%) m.p. 96°-98° C

Sources & evidence

ORD record
ord-9d714760a014484fa474acd54d904c79
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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