Acetyl chloride → HCID 67336483, compound

HRID 1670552Notes

Reaction equation

HRID 1670552 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][S:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)(=O)C>C(O)C>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[CH2:20][S:21][C:22]1[NH:26][CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67336269HCID 67336269, compound

Product 1

HCID 67336483HCID 67336483, compoundYield 204%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (10.11 g, 25.65 mmol) in absolute ethanol (125 mL). Add acetyl chloride (20.13 g, 256.5 mmol) dropwise. On addition, the reaction mixture exotherms to 40-50° C. Stir the reaction at 50 to 60° C. for 2.5 h. Cool the mixture to 0 to ° 5 C. Filter, wash with ethanol, and dry solid in vacuo to obtain 7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (8.64 g). MS (ES+) m/z: 294.3 (M+H)+.

Workup

  1. additionOn addition
  2. customexotherms to 40-50° C
  3. customthe reaction at 50 to 60° C. for 2.5 h
  4. temperatureCool the mixture to 0 to ° 5 C
  5. filtrationFilter
  6. washwash with ethanol
  7. customdry solid in vacuo

Sources & evidence

ORD record
ord-96fdf21f5908434b88a0889c963c8bd2
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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