Sulfuric Acid → HCID 23287875, compound

HRID 1637173Notes

Reaction equation

HRID 1637173 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[O:17][CH2:18][O:19][C:20]3[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=3[N:22]([C:23](=O)[CH2:24][CH2:25][Cl:26])[C:15]=2[CH:14]=1>O1CCCC1>[Cl:12][C:13]1[CH:33]=[CH:32][C:16]2[O:17][CH2:18][O:19][C:20]3[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=3[N:22]([CH2:23][CH2:24][CH2:25][Cl:26])[C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 23287870HCID 23287870, compound

Product 1

HCID 23287875HCID 23287875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of lithium aluminium hydride (3.0 g, 79 mmol) in dry tetrahydrofuran (80 ml), concentrated sulfuric acid (3.87 g, 39.5 mmol) was added dropwise at a rate to maintain a temperature <12° C. The mixture was stirred at room temperature for 1.5 h. A solution of the above amide (12.8 g, 37.8 mmol) in dry tetrahydrofuran (80 ml) was added dropwise and stirring was continued for 2 h. The reaction was quenched by careful addition of ethyl acetate (100 ml) followed by water (5.7 ml). Filtration of the mixture and evaporation of the filtrate in vacuo afforded 2-chloro-12-(3-chloropropyl)-12H-dibenzo[d,g][1,3,6]dioxazocine as a foam.

Workup

  1. additionwas added dropwise at a rate
  2. temperatureto maintain a temperature <12° C
  3. stirringstirring
  4. waitwas continued for 2 h
  5. customThe reaction was quenched by careful addition of ethyl acetate (100 ml)
  6. filtrationFiltration of the mixture and evaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-933f6a20677a4f4bb76a3e8c98a2259b
Source dataset
uspto-grants-2000_03
Patent number
US06040302

Reaction notes

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