Triethylamine → HCID 66614061, compound

HRID 1402676Notes

Reaction equation

HRID 1402676 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH2:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH2:20][CH3:21]>ClCCl>[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH:11][C:19](=[O:22])[CH2:20][CH3:21])[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 666106712-Bromo-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amine

Product 1

HCID 66614061HCID 66614061, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-Bromo-4,5,6,7-tetrahydro-benzothiazol-6-ylamine (0.36 grams, 1.5 mmol, obtained in above step) and triethylamine (0.43 mL, mmol) in dichloromethane (15 mL) was cooled to 0° C. Propionylchloride (0.17 mL, 1.8 mmol) in dichloromethane (2 mL) were added and stirred the reaction mass for 30 minutes. After completion of reaction, the mass was poured onto ice cold water and the product was extracted with ethyl acetate (3×15 mL). The combined organics were washed with water followed by brine, dried over anhydrous sodium sulphate and the organic volatiles were evaporated under vacuum. The residue was purified by flash chromatography (methanol/chloroform, 2/98) to obtain the title compound (0.4 grams).

Workup

  1. customAfter completion of reaction
  2. additionthe mass was poured onto ice cold water
  3. extractionthe product was extracted with ethyl acetate (3×15 mL)
  4. washThe combined organics were washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customthe organic volatiles were evaporated under vacuum
  7. customThe residue was purified by flash chromatography (methanol/chloroform, 2/98)

Sources & evidence

ORD record
ord-1d1edd963fb74a17ade6eae3f37399bc
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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