4-Amino-1-butanol → HCID 21878469, compound

HRID 723956Notes

Reaction equation

HRID 723956 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].Cl[C:8]1[S:9][C:10]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1.C(N(C(C)C)CC)(C)C.N.CO>O.C(Cl)Cl.CN(C=O)C>[N+:17]([C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])[S:9][C:10]=2[CH:16]=1)([O-:19])=[O:18]

Participants

8

Reactant 4

HCID 258684-Amino-1-butanolHCID 754762-Chloro-6-nitrobenzothiazoleHCID 81531DiisopropylethylamineHCID 21705897Ammonia methanol

Product 1

HCID 21878469HCID 21878469, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In an oven fried vial charged with 4-amino-1-butanol (172 μl, 2 eq.), 2-chloro-6-nitro-benzothiazol (200 mg, 0.93 mmol) and diisopropyl-ethylamine (1 mL) was added DMF (5 mL). The dark brown mixture was heated at 100° C. for 2 hours. After cooling, the mixture was diluted with 20 mL of water and extracted with ethyl-acetate (50 mL). The ethyl acetate layer was washed with brine, dried over MgSO4 and then evaporated to give a dark residue. This residue was subjected to silica gel chromatography (7% 2M ammonia/methanol in CH2Cl2) to give the desired product (45 mg, 18%). 1H NMR (CD3OD) δ: 8.55 (d, 1H, J=2.3 Hz), 8.17 (dd, 1H, J=2.3, 8.9 Hz), 7.47 (d, 1H, J=8.9 Hz), 3.63 (m, 3H), 3.53 (t, 2H, J=6.8 Hz), 1.80–1.75 (m, 2H), 1.70–1.65 (m, 2H); MS (M+1, 268).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl-acetate (50 mL)
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give a dark residue

Sources & evidence

ORD record
ord-b03448c585c044dc86ef41d0a0bae58c
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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