Ammonium Chloride → HCID 12822421, compound

HRID 355258Notes

Reaction equation

HRID 355258 reaction equation
[N:1]([CH2:4][C@H:5]1[C@H:8]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:7][C:6]1=[O:29])=[N+]=[N-].[Cl-].[NH4+]>CO.[Zn]>[NH2:1][CH2:4][C@H:5]1[C@H:8]([S:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:7][C:6]1=[O:29]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 12822398HCID 12822398, compound

Product 1

HCID 12822421HCID 12822421, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of trans 3-azidomethyl-4-tritylthio-2-azetidinone (10.0 g, 47.5 mmol) in dry methanol (500 ml) was added ammonium chloride (19.0 g) and zinc powder (1.0 g) and the suspension was stirred at room temperature for 5 h. The reaction mixture was filtered and evaporated. The residue was partitioned between 1N hydrochloric acid and benzene. The aqueous layer was basified with 1M sodium bicarbonate and extracted with methylene chloride. The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The crude amine crystallized from ether, 14.05 g (79%); mp 139°-139.5° C.; Anal. calcd for C23H22N2OCl.1/4 CH2Cl2 : C 70.56, H 5.73, N 7.08; Found: C 70.68, H 5.94, N 7.27; ir (CHCl3) νmax : 3400 and 1760 cm-1 ; 1Hmr (CDCl3) δ: 7.35 (15H, m), 5.15 (1H, m), 4.3 (1H, bs), 2.7-3.5 (3H, m) and 1.3 ppm (2H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customThe residue was partitioned between 1N hydrochloric acid and benzene
  4. extractionextracted with methylene chloride
  5. washThe extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe crude amine crystallized from ether, 14.05 g (79%)

Sources & evidence

ORD record
ord-094f54ed5fd844c89e4f9b1e9dde853a
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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