Water → HCID 178509706, compound

HRID 2214763Notes

Reaction equation

HRID 2214763 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[N:12]=1.[Br:21]Br.O.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:21][SH:9]1[CH:10]=[C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[N:12]=[C:8]1[NH:7][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24408BromineHCID 21948399HCID 21948399, compound

Product 1

HCID 178509706HCID 178509706, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[2-(Pyrazin-2-ylamino)-thiazol-4-yl]-benzonitrile (1.5 g, 5.36 mmol) is suspended in hot glacial acetic acid (10 ml) and bromine (0.275 ml) is added dropwise at room temperature with stirring. The resultant suspension is stirred at room temperature for 10 minutes. Water (ca. 100 ml) is added to the mixture, which is basified to pH 9 with solid potassium carbonate. The resulting precipitate is filtered and washed with water to yield 3-[S-bromo-2-(pyrazin-2-ylamino)-thiazol-4-yl]-benzonitrile, m.p. 215° C. (dec.), m.s. 279 (ES+, M+—Br).

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-42a4853903c74d7ab9868de6d54e2440
Source dataset
uspto-grants-2006_09
Patent number
US07109202B2

Reaction notes

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