2-[[(2,3-Difluorophenyl)methyl]thio]-4,6-pyrimidinediamine → 2-[[(2,3-Difluorophenyl)methyl]thio]-5-nitroso4,6-pyrimidinediamine

HRID 497728Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH2:17])[CH:14]=[C:13]([NH2:18])[N:12]=1.[N:19]([O-])=[O:20].[Na+]>C(O)(=O)C.O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:12]=[C:13]([NH2:18])[C:14]([N:19]=[O:20])=[C:15]([NH2:17])[N:16]=1

Participants

Conditions

Temperature: 5 °C

Procedure

The product of example 2, step (a) (2.5 g) was dissolved in acetic acid (150 ml) and the solution cooled to 5° C. A solution of sodium nitrite (625 mg) in water (50 ml) was added dropwise resulting in a dark blue colouration. The reaction was stirred at room temperature for 30 minutes during which time a pink solid precipitated from solution. This was isolated by filtration and washed with water, then dried at 50° C. to give the sub-titled product as a blue solid (4.14 g)

Workup

customresulting in a dark blue colouration
customprecipitated from solution
customThis was isolated by filtration
washwashed with water
customdried at 50° C.

Sources & evidence

ORD record: ord-6790d32f6d2549e2a73e491e4bf96eb7
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949643B2

Reaction notes

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