Trityl chloride → HCID 13179945, compound

HRID 370537Notes

Reaction equation

HRID 370537 reaction equation
C(N(CC)CC)C.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:28][C:29]1[CH:33]=[C:32]([CH3:34])[O:31][N:30]=1>C(Cl)Cl>[C:8]([NH:28][C:29]1[CH:33]=[C:32]([CH3:34])[O:31][N:30]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 661723-Amino-5-methylisoxazole

Product 1

HCID 13179945HCID 13179945, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (10 ml., 71.9 mmol) is added dropwise to an ice cold solution of 20.0 g. (71.6 mmol) of trityl chloride in 200 ml. of methylene chloride and the resulting solution is stirred at ice bath temperature for 5 minutes. 3-Amino-5-methylisoxazole (7.0 g., 71.5 mmol) in 50 ml. of methylene chloride is then added dropwise over 10 minutes. After the addition, the ice bath is removed and the stirring continued for 1.5 hours. The solution is washed with ice cold 1N HCl, dried (MgSO4) and the solvent concentrated under reduced pressure until a white solid is present. Diethyl ether is added and the solid collected and dried to give 21 g. (85%) of the title compound as a white crystalline material; m.p. 196°-199° C.

Workup

  1. additionAfter the addition
  2. customthe ice bath is removed
  3. washThe solution is washed with ice cold 1N HCl
  4. dry with materialdried (MgSO4)
  5. concentrationthe solvent concentrated under reduced pressure until a white solid
  6. additionDiethyl ether is added
  7. customthe solid collected
  8. customdried
  9. customto give 21 g

Sources & evidence

ORD record
ord-3ee628122cde41ac9d8ab264f2f1d9f8
Source dataset
uspto-grants-1985_07
Patent number
US04526977

Reaction notes

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