Triethylamine → HCID 67557400, compound

HRID 1415680Notes

Reaction equation

HRID 1415680 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].C(N(CC)CC)C.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>ClCCl>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C@@H:2]2[C:7]3[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=3[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]2[OH:16])=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 67557400HCID 67557400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-4-amino-6cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol (1.0 g), triethylamine (0.64 mL) and dichloromethane was added 4-chlorobenzoyl chloride (0.55 mL). The solution was stirred for a further 1.5 hours. The solution was washed with water and brine and dried over anhydrous magnesium sulphate. The solution was filtered and evaporated and recrystallised from ethyl acetate--60-80° petroleum ether as a white solid of mp 226-229° C.

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationThe solution was filtered
  4. customevaporated
  5. customrecrystallised from ethyl acetate--60-80° petroleum ether as a white solid of mp 226-229° C.

Sources & evidence

ORD record
ord-0b2c3e3988a848aca1c34394700a003b
Source dataset
uspto-grants-1999_06
Patent number
US05908860

Reaction notes

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