Tetrahydrofuran → 1,2,3,4-Tetrahydro-benzo(b)azepin-5-one

HRID 1404947Notes

Reaction equation

HRID 1404947 reaction equation
S1C(S)=CC2C=CC=CC1=2.[H-].[Na+].ClC[C:15]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)=O.C1C[O:30]CC1>>[NH:17]1[CH2:15][CH2:18][CH2:19][C:20](=[O:30])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]1=2

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 11073791Benzo[b]thiophene-2-thiol

Product 1

HCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-one

Procedure

Crude compound 72 (0.71 g, 4.3 mmol) was dissolved in 40 mL of dry THF under N2, stirred for 30 min at RT and then cooled down to 0° C. NaH (60% in mineral oil, 0.224 g, 5.5 mmol) was added to the ice-cold solution which became a yellowish suspension. The formed suspension was stirred for 40 min at 0° C. and then 2-chloro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone (0.89 g, 4.3 mmol) was added as a solution in 4 mL of dry THF. The reaction mixture was stirred at RT for 16 h. The work-up, the same as for compound 5, gave crude material which was purified by flash chromatography (CH2Cl2/EtOAc) giving 0.56 g of the crude product. Pumping the crude product under high vacuum over P4O10 at 45° C. for 4 h removed the co-crystallized EtOAc to yield the desired product 73 (36%): MS: m/z+ 340.1 [M+H]+; Anal. Calcd (found) for C19H17NOS2: C, 67.22 (67.18); H, 5.05 (5.11); N, 4.13 (4.08); S, 18.89 (18.70).

Workup

  1. temperaturecooled down to 0° C
  2. stirringThe formed suspension was stirred for 40 min at 0° C.
  3. stirringThe reaction mixture was stirred at RT for 16 h

Sources & evidence

ORD record
ord-05201c48271a431890f0e5ad1a715dc0
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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