Ammonia → HCID 21882838, compound

HRID 722135Notes

Reaction equation

HRID 722135 reaction equation
[NH3:1].[OH-].[NH4+:3].[Cl-].[NH4+].[C-:6]#N.[Na+].[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:27][CH:26]3[C:28](=O)[CH:23]([CH2:24][CH2:25]3)[CH2:22][C:21]=2[CH:30]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[NH2:1][C:28]1([C:6]#[N:3])[CH:23]2[CH2:24][CH2:25][CH:26]1[CH2:27][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:30][C:21]=1[CH2:22]2

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 21882780HCID 21882780, compound

Product 1

HCID 21882838HCID 21882838, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol (1 litre) saturated with ammonia cooled to 0° C. were added ammonium hydroxide (60.4 ml), ammonium chloride (30 g), sodium cyanide (3 g) and 2-benzyloxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[α][8]annulen-11-one (9.5 g). The reaction was stirred vigorously for 1 hr to ensure complete dissolution and left standing at 3° C. for 18 hrs. The precipitate was filtered, washed with ice-chilled water, ice-chilled methanol and dried in vacuo at 50° C. to give the title compound (8.4 g, 81%) as a white solid (360 MHz δd6-DMSO) 1.17 (2H, m), 1.84 (2H, m), 2.38 (2H, m), 2.78 (2H, m), 3.40 (2H, m), 5.03 (2H, s), 6.73 (2H, m), 6.98 (1H, d, J=8.2), 7.37 (5H, m). Step 3: [6S/R,9R/S,11R/S] 2′,3′,4′,5,5′,6,7,8,9,10-decahydro-2-benzyloxy-spiro [6,9-methanobenzocyclooctene-11,3′-[1,2,5]thiadiazole]1′,1′-dioxide.

Workup

  1. dissolutiondissolution
  2. waitleft
  3. waitstanding at 3° C. for 18 hrs
  4. filtrationThe precipitate was filtered
  5. washwashed with ice-
  6. temperaturechilled water, ice-
  7. temperaturechilled methanol
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-414870bf7bc24723a8d42745efaa8a6b
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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