4-Chlorophenyl Isocyanate → HCID 53710164, compound

HRID 274814Notes

Reaction equation

HRID 274814 reaction equation
[NH2:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>ClCCl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:1][CH:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]([OH:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:26])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 222432-Amino-1,2-diphenylethanol

Product 1

HCID 53710164HCID 53710164, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (-)-[R-(R*,S*)]-2-amino-1,2-diphenylethanol (1.0 g, 4.7 mmol) in dichloromethane (10 mL) is added dropwise a solution of 4-chlorophenyl isocyanate (0.72 g, 4.7 mmol) in dichloromethane (5 mL). The resulting mixture is stirred 1 hour at room temperature before filtering off the solid product and washing with CH2Cl2 (2X). The product is dried in vacuo at 114° C. to provide 1.4 g (81%) of desired product, mp 198° C. IR (KBr): 3327, 1665, 1549, 1234, 703 cm-1 ; NMR (DMSO-d6): 4.95 (m, 1H), 5.74 (m, 1H), 6.84-7.5 (m, 16H, 8.84 (S, 1H). Analysis calculated for C21H19ClN2O2.0.42H2O: C, 67.37; H, 5.34; N, 7.48. Found: C, 67.36; H, 5.16; N, 7.61.

Workup

  1. filtrationbefore filtering off the solid product
  2. washwashing with CH2Cl2 (2X)
  3. customThe product is dried in vacuo at 114° C.

Sources & evidence

ORD record
ord-fab1b6b9eb414598bd16026cba4b4ac2
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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