Ammonium Chloride → HCID 67559771, compound

HRID 1601152Notes

Reaction equation

HRID 1601152 reaction equation
[Cl-].[NH4+].[CH2:3]([C:7]1[N:8]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:28]([S:33]([NH:36][C:37]([NH:39][CH2:40][CH2:41][CH3:42])=[O:38])(=[O:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[C:9]([C:14](=[O:19])[CH2:15]S(C)=O)=[C:10]([S:12][CH3:13])[N:11]=1)[CH2:4][CH2:5][CH3:6]>C(O)C.[Zn]>[C:14]([C:9]1[N:8]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[C:28]([S:33]([NH:36][C:37]([NH:39][CH2:40][CH2:41][CH3:42])=[O:38])(=[O:34])=[O:35])=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:25][CH:26]=2)[C:7]([CH2:3][CH2:4][CH2:5][CH3:6])=[N:11][C:10]=1[S:12][CH3:13])(=[O:19])[CH3:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67561236HCID 67561236, compound

Product 1

HCID 67559771HCID 67559771, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

20 cm3 of a 10% aqueous solution of ammonium chloride and 650 mg of electrocyclic zinc are added to a solution of 1 g of the product obtained in Stage A above in 35 cm3 of ethanol. The resultant mixture is agitated for 24 hours then filtered, followed by evaporation, redissolving in ethyl acetate, washing with water, drying and evaporation. The residue is purified by passage over silica, eluting with methylene chloride with 2% methanol. 711 mg of expected product is obtained, melting at 176-177° C.

Workup

  1. filtrationthen filtered
  2. customfollowed by evaporation
  3. dissolutionredissolving in ethyl acetate
  4. washwashing with water
  5. customdrying
  6. customevaporation
  7. customThe residue is purified by passage over silica
  8. washeluting with methylene chloride with 2% methanol

Sources & evidence

ORD record
ord-1d694597f49e4ee7a4e4aa656f700916
Source dataset
uspto-grants-1999_11
Patent number
US05977155

Reaction notes

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