Trichloromethyl isocyanate → HCID 58203529, compound

HRID 2194773Notes

Reaction equation

HRID 2194773 reaction equation
ClC(Cl)(Cl)[N:3]=[C:4]=[O:5].[OH:8][CH2:9][CH2:10][N:11]1[C:16]([C:17]([C:19]2[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=2)[C:22]#[N:23])=[O:18])=[C:15]([CH:28]([CH3:30])[CH3:29])[C:14](=[O:31])[N:13]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[C:12]1=[O:41]>C(Cl)Cl>[C:22]([C:21]1[CH:20]=[C:19]([CH:26]=[C:25]([CH3:27])[CH:24]=1)[C:17]([C:16]1[N:11]([CH2:10][CH2:9][O:8][C:4](=[O:5])[NH2:3])[C:12](=[O:41])[N:13]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[C:14](=[O:31])[C:15]=1[CH:28]([CH3:30])[CH3:29])=[O:18])#[N:23]

Participants

4

Reactant 2

HCID 580152Trichloromethyl isocyanateHCID 58203528HCID 58203528, compound

Product 1

HCID 58203529HCID 58203529, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloro-isocyanato-methane (39 uL, 0.33 mmol, 2.0 eq) was added to 3-[3-(2-hydroxy-ethyl)-5-isopropyl-1-(4-methoxy-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile (76 mg, 0.165 mmol) in 2 mL of DCM. The reaction mixture was stirred at room temperature for 10 minutes. HPLC and LC-MS showed complete reaction of the starting materials. Ammonia gas was bubbled into 3 mL DCM in a test tube (keep bubbling for 5 minutes). The ammonia solution was added to the above reaction mixture. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered and concentrated down and purified (silica gel, 0-80% EtOAC/hexane) to give a white powder (42 mg, 51%). LC-MS shows 505.0 (M+1).

Workup

  1. customreaction of the starting materials
  2. customAmmonia gas was bubbled into 3 mL DCM in a test tube
  3. custom(keep bubbling for 5 minutes)
  4. additionThe ammonia solution was added to the above reaction mixture
  5. stirringThe reaction mixture was stirred at room temperature for 2 hours
  6. filtrationThe reaction mixture was filtered
  7. concentrationconcentrated down
  8. custompurified (silica gel, 0-80% EtOAC/hexane)

Sources & evidence

ORD record
ord-b9f392b1612042eda431491b41ba2c0a
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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