Aniline → HCID 68473353, compound

HRID 1514344Notes

Reaction equation

HRID 1514344 reaction equation
[CH2:1]([S:8][C:9]1[N:17]=[C:16]2[C:12]([NH:13][CH:14]=[N:15]2)=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CCCCO>[CH2:1]([S:8][C:9]1[N:17]=[C:16]2[C:12]([NH:13][CH:14]=[N:15]2)=[C:11]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 111617212-BENZYLTHIO-6-CHLOROPURINE

Product 1

HCID 68473353HCID 68473353, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Benzylthio-6-chloropurine (3.9 g) and aniline (3.42 g) in n-BuOH (100 ml) in the presence of triethylamine (7.5 ml) were refluxed for 2 h. Reaction mixture was cooled to room temperature, dried at a rotary vacuum evaporator, cooled with ice and 400 ml water was added with vigorous shaking. At standing overnight at −16° C. crude dark-brown solid was formed, which was dried into constant weight and chromatographically purified over 100 g silica packed in chloroform. The column was eluted with 500 ml 100% chloroform followed by 500 ml 1.25% MeOH/chloroform and then 1.5 L 2.5% MeOH/chloroform; 100 ml fractions collected and fractions 12 to 15 were dried to yield light-brown solid which were recrystallized from MeOH in the presence of active carbon. Yield 1.18 g of white, amorphous solid. TLC (2.5% MeOH/chloroform) shows only a single spot with no contaminants. HPLC purity: 98+%.

Workup

  1. customReaction mixture
  2. customdried at a rotary vacuum evaporator
  3. temperaturecooled with ice and 400 ml water
  4. additionwas added with vigorous shaking
  5. customcrude dark-brown solid was formed
  6. customwhich was dried into constant weight
  7. customchromatographically purified over 100 g silica
  8. washThe column was eluted with 500 ml 100% chloroform
  9. custom100 ml fractions collected
  10. customfractions 12 to 15 were dried
  11. customto yield light-brown solid which
  12. customwere recrystallized from MeOH in the presence of active carbon

Sources & evidence

ORD record
ord-7ac21f49301e44c2b8d627c3685c35ae
Source dataset
uspto-grants-2012_07
Patent number
US08222260B2

Reaction notes

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