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

HRID 34531Notes

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

Participants

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

customat ambient temperature
customThe solution obtained
filtrationwas filtered through celite and sodium bicarbonate
additionwas then added to the filtrate until no further precipitation
customThe precipitate was collected
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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