Thiophosgene → HCID 52914145, compound

HRID 531163Notes

Reaction equation

HRID 531163 reaction equation
[C:1]([CH2:4][N:5]1[CH2:18][CH2:17][CH2:16][N:15]2[CH2:19][CH:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=3)[CH2:21][N:8]([CH2:9][CH2:10][CH2:11][N:12]([CH2:30][C:31]([OH:33])=[O:32])[CH2:13][CH2:14]2)[CH2:7][CH2:6]1)([OH:3])=[O:2].[C:34](Cl)(Cl)=[S:35]>Cl.C(Cl)(Cl)Cl>[C:1]([CH2:4][N:5]1[CH2:18][CH2:17][CH2:16][N:15]2[CH2:19][CH:20]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]=[C:34]=[S:35])=[CH:27][CH:28]=3)[CH2:21][N:8]([CH2:9][CH2:10][CH2:11][N:12]([CH2:30][C:31]([OH:33])=[O:32])[CH2:13][CH2:14]2)[CH2:7][CH2:6]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 52914146HCID 52914146, compound

Product 1

HCID 52914145HCID 52914145, compoundYield 143%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of compound 28 (1.21 g, 1.75 mmol) in 0.5 M HCl (50 mL) was carefully added to thiophosgene (CSCl2) (4.03 mL, 6.04 g, 52.5 mmol) in CHCl3 (50 mL). The reaction mixture was stirred for 5 hours at room temperature and the layers were allowed to separate. The aqueous layer was removed and the organic CHCl3 layer was then washed with water (2×50 mL). The combined aqueous layers were washed with CHCl3 (3×50 mL) to remove unreacted thiophosgene. Finally, the aqueous layer was lyophilized to afford white crystalline solid 29 (1.26 g, 98% yield).

Workup

  1. customto separate
  2. customThe aqueous layer was removed
  3. washthe organic CHCl3 layer was then washed with water (2×50 mL)
  4. washThe combined aqueous layers were washed with CHCl3 (3×50 mL)
  5. customto remove unreacted thiophosgene

Sources & evidence

ORD record
ord-b13c4d9f96a040cea86e22658c7d2984
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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