Water → Methyl 4-(5-hexanamidobenzo[b]thien-3-ylmethyl)-3methoxybenzoate

HRID 1646347Notes

Reaction equation

HRID 1646347 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:31]=[CH:30][C:13]2[S:14][CH:15]=[C:16]([CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=3[O:28][CH3:29])[C:12]=2[CH:11]=1.CN1CCOCC1.O>ClCCl>[C:1]([NH:9][C:10]1[CH:31]=[CH:30][C:13]2[S:14][CH:15]=[C:16]([CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=3[O:28][CH3:29])[C:12]=2[CH:11]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 67340Hexanoyl chlorideHCID 14763113Methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365890Methyl 4-(5-hexanamidobenzo[b]thien-3-ylmethyl)-3methoxybenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hexanoyl chloride (0.024 g.) was added to a stirred solution of methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate (H) (0.06 g.), and N-methylmorpholine (0.1 ml.) in dichloromethane (3 ml.). The mixture was stirred for 1 hour and then poured into water (20 ml.). The aqueous mixture was extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4), and evaporated. The mixture was recrystallized from a mixture of ethyl acetate and hexane to give the title compound (0.05 g., 75%) as a colorless solid: NMR (250 MHz, DMSO-d6): 0.87 (t,3 H, CH2CH3), 1.28 (m,4 , CH2.CH2.CH3), 1.59 (quintet,2 H, CH2CH2CON), 2.29 (t,2 H, CH2CON), 3.84 (s, 3 H, OCH3), 3.91 (s,3 H, OCH3), 4.11 (s,2 H, CH 2 --Ar), 7.14 (d,1 H), 7.34 (s,1 H), 7.49 (m,3 H), 7.86 (d,1 H), 8.11 (d, 1 H), 9.95 (s,1 H).

Workup

  1. extractionThe aqueous mixture was extracted with dichloromethane (2×20 ml.)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe mixture was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9d34e0d4715a4f7fa2be05d137ff1665
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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