Bicarbonate Ion → HCID 18473541, compound

HRID 429803Notes

Reaction equation

HRID 429803 reaction equation
[CH:1]1([C:4]2[NH:12][C:11]3[C:10](=S)[NH:9][C:8](=[S:14])[N:7]([CH2:15][CH2:16][CH3:17])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)CCC(C(C)C)C(O)C1.C(=O)(O)[O-]>>[CH:18]1([NH:23][C:10]2[C:11]3[NH:12][C:4]([CH:1]4[CH2:3][CH2:2]4)=[N:5][C:6]=3[N:7]([CH2:15][CH2:16][CH3:17])[C:8](=[S:14])[N:9]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 4

HCID 769Bicarbonate IonHCID 1254MentholHCID 2906CyclopentylamineHCID 10934421HCID 10934421, compound

Product 1

HCID 18473541HCID 18473541, compound

Procedure

5.33 g (20 mmoles) of 8-cyclopropyl-3-n-propyl-2,6-dithioxantine and 42 ml of cyclopentylamine were heated in a 450 ml pressure reactor to 150° C. (50 psi) with the exclusion of air. After 20 hours the solution was transferred with menthol to a round bottom flask and evaporated in vacuo to dryness. The residue is treated with 60 ml of water and 5N HCl to obtain a pH of 2. The suspension is neutralized with bicarbonate to pH 7, the solid collected, washed, dried, suspended in refluxing acetone and collected again: 5.98 g of thioisoguanine with mp 274-6° C. (decomp).

Workup

  1. customevaporated in vacuo to dryness
  2. additionThe residue is treated with 60 ml of water and 5N HCl
  3. customto obtain a pH of 2
  4. customthe solid collected
  5. washwashed
  6. customdried
  7. temperaturein refluxing acetone
  8. customcollected again

Sources & evidence

ORD record
ord-885f933a31d248f6b6e4ab3e4df96001
Source dataset
uspto-grants-2001_11
Patent number
US06319928B1

Reaction notes

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