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Acetic Acid → 6-Benzothiazoleacetonitrile, 2-amino-alpha-methyl-

HRID 34531
Notes
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Reaction equation

HRID 34531 reaction equation
BrBr.C(O)(=O)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:17])[C:15]#[N:16])=[CH:10][CH:9]=1.[S-:18][C:19]#[N:20].[K+]>O>[NH2:20][C:19]1[S:18][C:13]2[CH:12]=[C:11]([CH:14]([CH3:17])[C:15]#[N:16])[CH:10]=[CH:9][C:8]=2[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24408BromineHCID 1200112-(4-Aminophenyl)propiononitrileHCID 516872Potassium thiocyanate

Product 1

HCID 134779396-Benzothiazoleacetonitrile, 2-amino-alpha-methyl-Yield 56%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
50 °C

Procedure

27.4 g of bromine in 87.5 ml of 95% v/v acetic acid were added dropwise to a stirred mixture of 25 g of 2-(p-aminophenyl)propionitrile [British Pat. No. 1,198,212], 66.8 g of potassium thiocyanate and 300 ml of 95% v/v acetic acid at ambient temperature. The mixture was then stirred at 50° C. for a further 2 hours before being poured into 1.5 liters of water. The solution obtained was filtered through celite and sodium bicarbonate was then added to the filtrate until no further precipitation occurred. The precipitate was collected and crystallized from methanol/water to give 19.4 g (56%) of 2-amino-α-methyl benzothiazole-6-acetonitrile as yellow prisms melting at 165.1° C.

Workup

  1. customat ambient temperature
  2. customThe solution obtained
  3. filtrationwas filtered through celite and sodium bicarbonate
  4. additionwas then added to the filtrate until no further precipitation
  5. customThe precipitate was collected
  6. customcrystallized from methanol/water

Sources & evidence

ORD record
ord-c226167e48ef43748913a30018a7cb36
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04762840

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes