Trityl chloride → HCID 70604455, compound

HRID 1730314Notes

Reaction equation

HRID 1730314 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]1[C:20](=[O:21])[N:12]2[CH:13]([C:18]#[N:19])[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12.[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([C:28]([NH:9][CH:10]2[C:20](=[O:21])[N:12]3[CH:13]([C:18]#[N:19])[C:14]([CH3:16])([CH3:17])[S:15][C@H:11]23)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 70604618HCID 70604618, compound

Product 1

HCID 70604455HCID 70604455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (44.5 g., 0.44 mole) is added to a slurry of 6-amino-2,2-dimethyl-3-cyanopenam hydrochloride (46.6 g., 0.2 mole) in methylene chloride (1500 ml.) at room temperature and the resulting mixture stirred for 20 minutes. Triphenylmethyl chloride (66.9 g., 0.24 mole) is added in one portion to the mixture which is stirred at room temperature for 3.5 hours. The methylene chloride layer is separated and washed with water (5 × 100 ml.). It is then dried (Na2SO4) and concentrated in vacuo to orange-red viscous oil. Methanol (50 ml.) is added and the mixture stirred for a half hour to give a yellow-white solid. The solid is filtered, resuspended in fresh methanol, and the suspension stirred for a half hour. The solid is recovered by filtration and dried in a vacuum oven at room temperature. Yield of crude = 47 gms. M.p. 116°-119° C.

Workup

  1. stirringis stirred at room temperature for 3.5 hours
  2. customThe methylene chloride layer is separated
  3. washwashed with water (5 × 100 ml.)
  4. dry with materialIt is then dried (Na2SO4)
  5. concentrationconcentrated in vacuo to orange-red viscous oil
  6. additionMethanol (50 ml.) is added
  7. stirringthe mixture stirred for a half hour
  8. customto give a yellow-white solid
  9. filtrationThe solid is filtered
  10. stirringthe suspension stirred for a half hour
  11. filtrationThe solid is recovered by filtration
  12. customdried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-dee188c218b240019bceb4fd298ffa7b
Source dataset
uspto-grants-1976_11
Patent number
US03992394

Reaction notes

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