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

HRID 1723214Notes

Reaction equation

HRID 1723214 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][CH:7]=[C:8]([CH2:9][C:10]3[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=3[O:20][CH3:21])[C:4]=2[CH:3]=1.CN1[CH2:30][CH2:29][O:28]CC1.O>ClCCl>[C:29]([NH:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][CH:7]=[C:8]([CH2:9][C:10]3[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=3[O:20][CH3:21])[C:4]=2[CH:3]=1)(=[O:28])[CH2:30][CH2:23][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 79724-MethylmorpholineHCID 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 chloridc (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,3H, CH2CH3), 1.28(m,4H, CH2.CH2.CH3), 1.59 (quintet,2H, CH2CH2CON), 2.29(t,2H, CH2CON), 3.84(s, 3H, OCH3), 3.91(s,3H, OCH3), 4.11(s,2H, CH2 -Ar), 7.14 (d,1H), 7.34 (s,1H), 7.49(m,3H), 7.86(d,1H), 8.11(d, 1H), 9.95(s,1H).

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-efca288449424897a0544489f88c0e06
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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