Dichloromethane → Trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(N-methylureido)-2H-1-benzopyran-3-ol

HRID 482709Notes

Reaction equation

HRID 482709 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:18]=[C:19]=[O:20].Cl[CH2:22]Cl>>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:14])([CH3:15])[C@@H:3]([OH:16])[C@H:2]([N:1]([CH3:22])[C:19]([NH2:18])=[O:20])[C:7]=2[CH:8]=1)#[N:13]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 12228Methyl IsocyanateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 67831194Trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(N-methylureido)-2H-1-benzopyran-3-ol

Procedure

Trans-4-amino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol (2.00 g) in dichloromethane (30 ml) was added dropwise to a stirred solution of methyl isocyanate (0.54 ml) in dichloromethane (15 ml), the temperature being maintained at below 10° C. After 15 min a white precipitate formed and the reaction mixture was allowed to reach room temperature. The solid was filtered and recrystallised from dichloromethane to give the title compound (1.30 g) as crystals of m.p. 143°-146° C.

Workup

  1. temperaturethe temperature being maintained at below 10° C
  2. customAfter 15 min a white precipitate formed
  3. customto reach room temperature
  4. filtrationThe solid was filtered
  5. customrecrystallised from dichloromethane

Sources & evidence

ORD record
ord-aec2cfa21ea043fbabb84b88ce05020c
Source dataset
uspto-grants-1986_03
Patent number
US04575511

Reaction notes

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