Benzene → HCID 13746074, compound

HRID 2290921Notes

Reaction equation

HRID 2290921 reaction equation
[CH3:1][O:2][C:3]1[C:10]2[CH:9]=[C:8]([C:11]([OH:13])=O)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:14][CH3:15].C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[CH2:28]([NH2:31])[CH:29]=[CH2:30]>O.C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:10]2[CH:9]=[C:8]([C:11]([NH:31][CH2:28][CH:29]=[CH2:30])=[O:13])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:14][CH3:15]

Participants

8

Reactant 4

HCID 241BenzeneHCID 7853AllylamineHCID 65578Oxalyl chlorideHCID 13746073HCID 13746073, compound

Product 1

HCID 13746074HCID 13746074, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3,4-dimethoxybenzocyclobutene-1-carboxylic acid and 400 mL benzene was stirred under N2 at 0° as oxalyl chloride (40.6 mL, 0.47 mole) was added dropwise. The reaction mixture was stirred for 2 hours at room temperature, then solvents were evaporated. Benzene was added and evaporated. The acid chloride was dissolved in CH2Cl2 (200 mL) and was added dropwise to a stirred, 0° solution of allylamine (8.5 mL, 0.11 mole), triethylamine (59 mL), and CH2Cl2 (212 mL). The reaction mixture was stirred for 1 hour at room temperature, then water was added. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with 1N HCl, saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated (in-vacuo) to yield 19.8 g cream colored solid, (84%); mp 98°-9°; M+ 247.

Workup

  1. additionwas added dropwise
  2. customsolvents were evaporated
  3. additionBenzene was added
  4. customevaporated
  5. dissolutionThe acid chloride was dissolved in CH2Cl2 (200 mL)
  6. stirringThe reaction mixture was stirred for 1 hour at room temperature
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with CH2Cl2
  9. washThe combined organic layers were washed with 1N HCl, saturated aqueous NaHCO3, saturated aqueous NaCl
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated (in-vacuo)
  13. customto yield 19.8 g cream colored solid, (84%)

Sources & evidence

ORD record
ord-e44909d0d66a4b36a513f7830467264f
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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