Hydrochloric Acid → (2R,2'R)-2,2'-{Dithiobis[(2-chloro[1,3]thiazolo[4,5-d]pyrimidine-5,7-diyl)(methylimino)]}dipentan-1-ol

HRID 2422195Notes

Reaction equation

HRID 2422195 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:17])[C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.[ClH:20].N([O-])=O.[Na+]>C(#N)C.O>[Cl:20][C:2]1[S:3][C:4]2[C:9]([N:10]([C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])[CH3:17])=[N:8][C:7]([S:18][S:18][C:7]3[N:8]=[C:9]([N:10]([C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])[CH3:17])[C:4]4[S:3][C:2]([Cl:20])=[N:19][C:5]=4[N:6]=3)=[N:6][C:5]=2[N:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178448297HCID 178448297, compound

Product 1

HCID 59868834(2R,2'R)-2,2'-{Dithiobis[(2-chloro[1,3]thiazolo[4,5-d]pyrimidine-5,7-diyl)(methylimino)]}dipentan-1-olYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(2R)-2-[(2-Amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)(methyl)amino]pentan-1-ol (1.0 g, 3.34 mmol) was dissolved in acetonitrile (25 ml) and concentrated hydrochloric acid (40 mL). Sodium nitrite (461 mg, 6.67 mmol) was dissolved in water (2 mL) and added at 0° C. The reaction mixture was kept at 0° C. for three days. The reaction mixture was poured onto ice and the precipitated product was collected by filtration and washed with water. Drying in vacuo gave the title compound 800 mg (75% yield).

Workup

  1. additionadded at 0° C
  2. additionThe reaction mixture was poured onto ice
  3. filtrationthe precipitated product was collected by filtration
  4. washwashed with water
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-8750b103fec046fc9fc3bc7b38384816
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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