Dimethylamine → 1,2-dihydro-4,4-dimethyl-9-(N,N-dimethylcarbamyloxy)-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran

HRID 1579098Notes

Reaction equation

HRID 1579098 reaction equation
[CH3:1][C:2]1([CH3:25])[C:7]2[S:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.[C:26](Cl)(Cl)=[O:27].[CH3:30][N:31](C)[C:32]1C=CC=CC=1.ClC([O-])=O.CNC>>[CH3:25][C:2]1([CH3:1])[C:7]2[S:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:24][C:26](=[O:27])[N:31]([CH3:32])[CH3:30])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1

Participants

6

Reactant 5

HCID 674DimethylamineHCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 2135232H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-4,4-dimethyl-HCID 21226386Carbonochloridate

Product 1

HCID 215579031,2-dihydro-4,4-dimethyl-9-(N,N-dimethylcarbamyloxy)-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran

Procedure

By reacting 1,2-dihydro-4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran with an equimolar amount of phosgene in the presence of dimethylaniline in a procedure similar to that described above in Example 20 and reacting the resulting chloroformate with dimethylamine, there is obtained 1,2-dihydro-4,4-dimethyl-9-(N,N-dimethylcarbamyloxy)-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran.

Sources & evidence

ORD record
ord-ea2e7484d8c04c258aafffff22741bd6
Source dataset
uspto-grants-1976_02
Patent number
US03940421

Reaction notes

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