2-Aminothiazole → [(2-Amino-1,3-thiazol-5-yl)sulfanyl]formonitrile

HRID 1363736Notes

Reaction equation

HRID 1363736 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[S-:7][C:8]#[N:9].[Na+].BrBr.[NH4+].[OH-]>CO.[Na+].[Br-]>[S:7]([C:4]1[S:3][C:2]([NH2:1])=[N:6][CH:5]=1)[C:8]#[N:9]

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 14923Ammonium HydroxideHCID 24408BromineHCID 516871Sodium thiocyanate

Product 1

HCID 3109677[(2-Amino-1,3-thiazol-5-yl)sulfanyl]formonitrileYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 253881Sodium BromideSolvent

Conditions

Temperature
0 °C

Procedure

2-Aminothiazole (35 g, 350 mmol) and sodium thiocyanate (89 g, 1.08 mol) in MeOH (400 mL) was stirred at −10° C. Bromine (18.0 mL, 350 mmol) dissolved in MeOH (100 mL) saturated with NaBr was slowly added keeping the internal temperature between −10 and 0° C. After the addition the mixture was stirred at 0° C. for 3H and the reaction mixture was poured into ice water (1500 mL). Aqueous NH4OH was added to pH ca 8.5 causing precipitation of light yellow crystals which were isolated by filtration, washed with ice water and dried in a vacuum oven to give 30 g (55%) 5-thiocyanato-thiazol-2-ylamine as light yellow crystals.

Workup

  1. additionwas slowly added
  2. customthe internal temperature between −10 and 0° C
  3. additionAfter the addition the mixture
  4. customprecipitation of light yellow crystals which
  5. customwere isolated by filtration
  6. washwashed with ice water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4f0dca8a6c474114a3162beffd47520b
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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