Butyryl chloride → HCID 21997649, compound

HRID 1977112Notes

Reaction equation

HRID 1977112 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12][CH2:13][C:14]#[N:15].C(N(C(C)C)CC)(C)C.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28]>ClCCl.CN(C1C=CN=CC=1)C>[C:14]([CH2:13][S:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:25](=[O:29])[CH2:26][CH2:27][CH3:28])#[N:15]

Participants

6

Reactant 3

HCID 8855Butyryl chloride2×HCID 81531DiisopropylethylamineHCID 21997632HCID 21997632, compound

Product 1

HCID 21997649HCID 21997649, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2-Amino-4-trifluoromethylphenylsulfanyl)acetonitrile (1.33 g) dissolved in dichloromethane (5 ml) was stirred on an ice bath at 0° C. Diisopropylethylamine (1 ml) and butyric acid chloride (0.9 ml) was added, and the resulting solution was allowed to reach room temperature. After 22 h more butyric acid chloride (0.9 ml) and DMAP (0.70 g) were added at 0° C. and stirring was continued at 40° C. for 24 h. The cold mixture was diluted with dichloromethane (20 ml), extracted with saturated aqueous sodium bicarbonate (10 ml), washed with water (2×50 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/heptane 1:1 as eluent. The title compound was obtained as a sirup. Yield 1.72 g (100%). The compound could be crystallised from ethyl acetate/heptane, mp 88.5-89.5° C.; El SP/MS: 302 (M+). 1H-NMR(CDCl3) δ (ppm): 8.85 (br, 1H), 8.38 (br, 1H), 7.28 (d, 1H), 7.38 (dd, 1H), 3.50 (s, 2H), 2.46 (t, 2H), 1.82 (sextet), 1.03 (t, 3H).

Workup

  1. customto reach room temperature
  2. stirringstirring
  3. extractionextracted with saturated aqueous sodium bicarbonate (10 ml)
  4. washwashed with water (2×50 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-48909e8b758f4f4ab96480167565baab
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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