Diisopropylethylamine → HCID 9945554, compound

HRID 1070428Notes

Reaction equation

HRID 1070428 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)C(C)C)(C)C.[C:20]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][C:23]([C:26](Cl)=[O:27])=[CH:22][CH:21]=1>ClCCl>[C:20]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:21]=[CH:22][C:23]([C:26]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[O:27])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 841514-Phenylbenzoyl chlorideHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Product 1

HCID 9945554HCID 9945554, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine of Step A (0.300 g) and N,N-diisopropylethyl amine (0.5 mL) in dichloromethane (25 mL) was cooled to 0°. To this was added a solution of 4-biphenyl carbonyl chloride (0.518 g) in dichloromethane (5 ml). The solution was stirred overnight as it warmed to room temperature, then washed with 0.1N hydrochloric acid, aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash chromatography of the residue on silica gel provided the title compound as a white solid (0.490 g), m.p. 164-166° C.

Workup

  1. washwashed with 0.1N hydrochloric acid, aqueous sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated to an oil

Sources & evidence

ORD record
ord-d288369e67174533afc18075c92b1a3e
Source dataset
uspto-grants-2005_06
Patent number
US06903091B2

Reaction notes

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