Triethylamine → N-(2-chlorophenyl)-N,8-dimethyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 1949982Notes

Reaction equation

HRID 1949982 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([OH:17])=O)[S:14][C:5]=3[C:4]=2[CH:3]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:19]([CH3:18])[C:15]([C:13]1[S:14][C:5]2[C:4]3[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:12]=1)=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 136736Benzenamine, 2-chloro-N-methyl-HCID 579005248-methyl-4H-thieno[3,2-c]chromene-2-carboxylic acid

Product 1

HCID 57900390N-(2-chlorophenyl)-N,8-dimethyl-4H-thieno[3,2-c]chromene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

8-Methyl-4H-thieno[3,2-c]chromene-2-carboxylic acid was converted to the acid chloride as in Example 3, then treated with N-methyl-2-chloroaniline (1.5 equiv), and triethylamine (5 equiv) in dichloromethane and N,N-dimethyl-4-aminopyridine (0.2 equiv) at 24° C. After about 24 hr, the reaction mixture was diluted with dichloromethane, and the resulting solution was washed with saturated aqueous sodium bicarbonate. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (5:2 hexanes/ethylacetate) provided 168bp. 1H (500 MHz, CDCl3) δ 7.53 (d, J=7.7 Hz, 1 H), 7.35-7.41 (m, 3 H), 6.97 (s, 1 H), 6.94 (d, J=8.2 Hz, 1 H), 6.76 (d, J=8.2 Hz, 1 H), 6.56 (s, 1 H), 5.00 (s, 2 H), 3.39 (s, 3 H), 2.26 (s, 3 H). LCMS (ESI) m/z: 370.1

Workup

  1. washthe resulting solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (5:2 hexanes/ethylacetate)
  6. customprovided 168bp

Sources & evidence

ORD record
ord-04458196134a4e27bf073c3bbeeda45a
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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