Chloroacetyl chloride → HCID 10205969, compound

HRID 1786528Notes

Reaction equation

HRID 1786528 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([NH2:25])[CH:5]=2.C(N(CC)C(C)C)(C)C.[Cl:35][CH2:36][C:37](Cl)=[O:38]>ClCCl.O.C(OCC)(=O)C>[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([NH:25][C:37](=[O:38])[CH2:36][Cl:35])[CH:5]=2

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 10294498HCID 10294498, compound

Product 1

HCID 10205969HCID 10205969, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,7-diamino-3-cyano-4-(3-bromo-4,5-dimethoxy phenyl)-4H-chromene (50 mg, 0.124 mmol) in dichloromethane (2 ml) was added N,N-diisopropylethylamine (0.043 ml, 0.247 mmol). The flask was cooled in iced water and a solution of chloroacetyl chloride (14 mg, 0.124 mmol) in dichloromethane (1 ml) was added dropwise. The reaction mixture was stirred for 3 h, diluted with ethyl acetate, then washed with water, brine and dried over anhydrous sodium sulfate, and evaporated. The resulting solid was washed with a small amount of dichloromethane to yield the title compound as a white solid in a yield of 24%. 1H NMR (DMSO-d6): 10.45 (s, 1H), 7.56 (s, 1H), 7.14-7.12 (m, 1H), 7.07 (s, 1H), 7.05 (s, 2H), 6.97 (s, 1H), 6.89 (d, J=0.9, 1H), 4.74 (s, 1H), 4.24 (s, 2H), 3.80 (s, 3H), 3.70 (s, 3H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. washThe resulting solid was washed with a small amount of dichloromethane

Sources & evidence

ORD record
ord-201c08821a414945bd087660652d455b
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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