Ammonia → HCID 70637607, compound

HRID 436812Notes

Reaction equation

HRID 436812 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[C:41](=[O:42])[N:23]3[CH:24]([C:29](Cl)=[N:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[NH3:46]>C(Cl)(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:41](=[O:42])[N:23]3[CH:24]([C:29](=[N:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[NH2:46])[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 86734829HCID 86734829, compound

Product 1

HCID 70637607HCID 70637607, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 13.1 g. (22 mmoles) of 6-(triphenylmethylamino)-2,2-dimethyl-3-{chloro-[N-(4-methoxybenzyl)imino]methyl}penam in 45 ml. of ethanol-free chloroform, a 1.33 N ammonia solution in chloroform is added all at once. The resulting mixture is stirred 5 minutes at 0° C. and then for 45 minutes at 25° C. The mixture is then filtered, and the filtrate rotoevaporated to an amber oil. Addition of ether (100 ml.) affords a precipitate which is filtered and then taken up in 150 ml. chloroform. The chloroform solution is washed first with 100 ml. 0.5N NaOH; and then with three 150 ml. portions of water. It is then dried over anhydrous sodium sulfate and rotoevaporated to afford the title compound as an orange foam. Rotoevaporation of the filtrate obtained after the ether precipitation procedure affords more of the title compound, as an orange foam. Total yield= 12.05 g. (95%). 1H--NHR (CDCl3 ) ppm (δ) 1.33 (3H, s, 2--CH3); 1.60 (3H, s, 2--CH3); 3.81 (3H, s, --OCH3); 4.17-4.68 (3H, m; 3-, 5- and 6-H); 4.24 (2H, s, --CH2 --), 4H, AB with Ha within 7.2-7.68 multiplet; Hb centered at 6.89, J= 9 HZ. (CH3O--C6H4 --), 7.2-7.68 (15H, m, C6H5). Infrared (CH2Cl2) λmax (μ) 5.62 (s, strong); 5.75-5.83 (broad s, strong); 5.97 (broad s, strong).

Workup

  1. customTo a 0° C.
  2. waitfor 45 minutes at 25° C
  3. filtrationThe mixture is then filtered
  4. additionAddition of ether (100 ml.)
  5. customaffords a precipitate which
  6. filtrationis filtered
  7. washThe chloroform solution is washed first with 100 ml
  8. dry with materialIt is then dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-399362f52fd742df86311b8c23e848c3
Source dataset
uspto-grants-1977_06
Patent number
US04028360

Reaction notes

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