Sulfuric Acid → HCID 20362673, compound

HRID 1679363Notes

Reaction equation

HRID 1679363 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH:12]([CH3:26])[C:13](=[O:25])[N:14]([CH2:16][CH2:17][O:18]C3CCCCO3)[CH2:15][C:9]=2[CH:8]=1>ClCCl>[Cl:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH:12]([CH3:26])[C:13](=[O:25])[N:14]([CH2:16][CH2:17][OH:18])[CH2:15][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20362669HCID 20362669, compound

Product 1

HCID 20362673HCID 20362673, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 ml. of 20% sulfuric acid are added, with vigorous stirring, to a solution of 2.9 g. (0.0086 moles) of 8-chloro-4-methyl-2-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one in 50 ml. of dichloromethane. When the addition is complete, stirring is continued for 2 at room temperature. After decantation, the organic phase is washed neutral with water, dried over anhydrous sodium sulfate and then evaporated to dryness in vacuo. The solid residue is purified by chromatography on a silica column and then by recrystallization from methanol. 8-Chloro-2-(2-hydroxyethyl)-4-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one is obtained in a yield of 10% of theory. M.P. 139°-140° C.

Workup

  1. additionWhen the addition
  2. customis continued for 2 at room temperature
  3. washAfter decantation, the organic phase is washed neutral with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe solid residue is purified by chromatography on a silica column
  7. customby recrystallization from methanol

Sources & evidence

ORD record
ord-c1e9f3e646f64c4b87b2d21b1d865f06
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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