Sulfuric Acid → HCID 178504584, compound

HRID 1391467Notes

Reaction equation

HRID 1391467 reaction equation
[Br:1][C:2]1[C:3]([OH:18])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[N-:19]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>C(Cl)Cl>[Br:1][C:2]1[C:3]([OH:18])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:17])(=[NH:19])=[O:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 178504606HCID 178504606, compound

Product 1

HCID 178504584HCID 178504584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

324 mg of (RS)-5-bromo-2-[4-(methylsulfinyl)phenylamino]pyrimidin-4-ol and 128 mg of sodium azide are suspended in 6 ml of methylene chloride and mixed drop by drop with 0.3 ml of concentrated sulfuric acid while being cooled with ice. The mixture is stirred for 36 hours at 40° C. The organic phase is decanted off, and the residue is stirred with ice water. The solid is suctioned off, washed twice with water and once with ethanol and dried. 266 mg (78.2% of theory) of the product with a melting point of 230° C. (decomposition) is obtained.

Workup

  1. temperaturewhile being cooled with ice
  2. customThe organic phase is decanted off
  3. stirringthe residue is stirred with ice water
  4. washwashed twice with water and once with ethanol
  5. customdried
  6. custom266 mg (78.2% of theory) of the product with a melting point of 230° C. (decomposition) is obtained

Sources & evidence

ORD record
ord-535a1d9e8b274420b80a60eddfc56b48
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

Loading…